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[ CAS No. 23357-46-2 ] {[proInfo.proName]}

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Chemical Structure| 23357-46-2
Chemical Structure| 23357-46-2
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Product Citations

Product Citations

Shilong Gao ; DOI:

Abstract: Primary amine is one of the most prevalent moieties in synthetic intermediates and pharmaceutical compounds. The preparation of aliphatic primary amines via C?H functionalization would provide direct access to the nitrogen-containing compounds from hydrocarbon substrates. While the enzymatic oxyfunctionalization of C–H bonds is well established, the analogous strategy for nitrogen incorporation is unknown in Nature. Likewise, a synthetic method for selective primary amination of aliphatic C–H bonds remains elusive. Combining chemical intuition and inspiration from Nature, chemists and protein engineers have created new heme-containing enzymes for the C(sp3)–H primary amination via directed evolution. This thesis describes some of the efforts in the continued pursuit of these new-to-nature reactions. Chapter I discusses directed evolution in the context of biocatalysis, the strategies for introducing new-to-nature chemistry in enzymes, the discovery of nitrene transferases from the cytochrome P450 monooxygenase, and finally, the development of C(sp3)–H primary aminases. Chapter II details the discovery and engineering of serine-ligated cytochrome P411 enzymes that catalyze the first primary amination of C(sp3)–H bonds with excellent selectivity, affording a broad scope of enantioenriched primary amines. Chapter III demonstrates that these new-to-nature nitrene transferases were engineered to aminate and amidate unactivated, unbiased C(sp3)–H bonds with unprecedented selectivity. In Chapter IV, engineered protoglobins are shown to utilize hydroxylamine (NH?OH) for nitrene transfer reactions, including benzylic C–H primary amination and styrene aminohydroxylation. Overall, these new-to-nature reactions can be considered the nitrogen analogs to the C–H oxidation chemistry performed by monooxygenases and peroxygenases. By offering a direct path from saturated precursors, these enzymes present a new biochemical logic for accessing nitrogen-containing compounds. Finally, this work hints at the possible future discovery of natural enzymes that use hydroxylamine precursors for amination chemistry.

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Product Details of [ 23357-46-2 ]

CAS No. :23357-46-2 MDL No. :MFCD00671629
Formula : C10H13N Boiling Point : -
Linear Structure Formula :- InChI Key :JRZGPXSSNPTNMA-SNVBAGLBSA-N
M.W : 147.22 Pubchem ID :7058072
Synonyms :

Calculated chemistry of [ 23357-46-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.58
TPSA : 26.02 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 1.72
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 1.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.847 mg/ml ; 0.00575 mol/l
Class : Soluble
Log S (Ali) : -1.88
Solubility : 1.93 mg/ml ; 0.0131 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.187 mg/ml ; 0.00127 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.84

Safety of [ 23357-46-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501 UN#:2735
Hazard Statements:H314 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 23357-46-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 23357-46-2 ]

[ 23357-46-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 23357-46-2 ]
  • [ 79-04-9 ]
  • [ 32908-45-5 ]
  • 2
  • [ 23357-46-2 ]
  • [ 814-49-3 ]
  • diethyl N-[(R)-1,2,3,4-tetrahydro-1-naphthyl]phosphoramidate [ No CAS ]
  • 3
  • [ 15761-39-4 ]
  • [ 23357-46-2 ]
  • [ 876623-95-9 ]
YieldReaction ConditionsOperation in experiment
Boc-L-Pro-OH (41.7 g, 0.17 mol), R-tetrahydronapthylamine (31.8g, 0.22 mol), and hydroxybenzotriazole (28.4g, 0.18 mol) was dissolved in dimethylformamide (30OmL) and cooled to 00C. To this cooled reaction mixture was added EDC (41.7 g, 0.22 mol) followed by DiPEA (30.ImL, 0.17 mol). Reaction was allowed to slowly warm to room temperature and was stirred overnight. Reaction mixture was then partitioned between ethyl acetate and water. The aqueous layer was discarded and the organic layer was washed sequentially with sat. NaHCU3, 0.5 N HCl, and brine. Dried over Na2SO4. Reaction was clean by TLC (50 % ethyl acetate / hexanes). Took crude on to next step. Dissolved crude in CH2Cl2 (200 mL) and TFA (200 mL). Within 15 minutes, reaction was baseline by TLC (50% ethyl acetate / hexanes). Removed most of solvent via rotary evaporation. Upon addition of diethyl ether, a white solid crashes out. Filtered solid and washed with diethyl ether. Dried solid under vacuum. Obtained 63 g of desired compound (95% yield over 2 steps). 1H NMR (CD3OH): consistent with proposed structure.
  • 4
  • [ 24424-99-5 ]
  • [ 23357-46-2 ]
  • (R)-1,2,3,4-tetrahydronaphth-1-yl carbamic acid tert-butyl ester [ No CAS ]
  • 5
  • [ 23357-46-2 ]
  • [ 109-94-4 ]
  • [ 922516-02-7 ]
YieldReaction ConditionsOperation in experiment
63% at 80℃; for 14h; A mixture of(R)-(-)-1,2,3,4-tetrahydro-1-naphthylamine (10.0 g, 67.9 mmol, 1 equiv) and ethylformate (6.23 mL, 77.4 mmol, 1.14 equiv) was heated to 80 C for 14 h. Hexanes was added and themixture was triturated by sonication, then filtered and rinsed with hexanes to yield the product (7.44 g,63%) as atan solid. R1= 0.22 (3:1 hexanes/EtOAc). ‘HNMR(400 MHz, CDC13) 3: 8.23 (s, 1H), 7.29-7.25 (m, 1H), 7.23-7.16 (m, 2H), 7.13-7.08 (m, 1H), 5.82 (bs, 1H), 5.28 (dd, 1H, J= 5.2, 14.0 Hz), 2.85-2.73 (m, 2H), 2.15-2.03 (m, 1H), 1.88-1.81 (m, 3H); ‘3C NMR (100 MHz, CDC13) 3: 160.5, 137.7, 136.1,129.4, 128.8, 127.6, 126.5, 46.4, 30.3, 29.3, 20.0. HRMS calcd for C,,H,3NONa: 198.0889, found198.0890.
at 60℃; (l/?)-l,2,3,4-Tetrahydro-l-naphthalenamine (5.0 g, 34 mmol) was heated in 15 mL of ethyl formate at 60 C overnight, during which time a precipitate formed. The reaction mixture was added to 100 mL of hexanes with stirring, and the resulting solids were filtered, washed with hexanes and dried to give 4.63 g of the formamide as white needles. The resulting formamide (4.54 g, 26 mmol) was dissolved in 50 mL of tetrahydrofuran and added dropwise to a suspension of lithium aluminum hydride (1.1 g, 29 mmol) in 20 mL of tetrahydrofuran that had been cooled to 0 C. The reaction mixture was refluxed overnight, then cooled to 0 C and quenched by the sequential addition of 1.1 mL of water, 1.1 mL of15 % aqueous NaOH solution and 3.3 mL of water. The mixture was stirred at ambient temperature for 30 minutes and diluted with ethyl acetate. Several grams of MgSO4 were added, and the mixture was filtered through Celite diatomaceous filter aid and concentrated under reduced pressure to give 4.0 g of the title compound as a colorless oil.1H NMR (CDCl3) δ 1.17 (s, IH), 1.65-2.0 (m, 4H), 2.47 (s, 3H), 2.65-2.85 (m, 2H), 3.63 (m,IH), 7.0-7.35 (m, 4H).
at 60℃; EXAMPLE 6 General preparation of 2-[1-[(substituted-phenyl)acetyl]-4-piperidinyl]-N-methyl-N-[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]-4-thiazolecarboxamide (Compound 144, Compound 145, Compound 146, Compound 147, Compound 148 and Compound 132) and N-methyl-2-[1-[[substituted-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]-4-thiazolecarboxamide (Compound 149 and Compound 150) Step A: Preparation of (1R)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine. (1R)-1,2,3,4-tetrahydro-1-naphthalenamine (5.0 g, 34 mmol) was heated in 15 mL of ethyl formate at 60 0C overnight, during which time a precipitate formed. The reaction mixture was added to 100 mL of hexanes with stirring, and the resulting solids were filtered, washed with hexanes and dried to give 4.63 g of the formamide as white needles. The resulting formamide (4.54 g, 26 mmol) was dissolved in 50 mL of tetrahydrofuran and added dropwise to a suspension of lithium aluminum hydride (1.1 g, 29 mmol) in 20 mL of tetrahydrofuran that had been cooled to 0 C. The reaction mixture was refluxed overnight, then cooled to 0 0C and quenched by the sequential addition of 1.1 mL of water, 1.1 mL of 15 % aqueous NaOH solution and 3.3 mL of water. The mixture was stirred at ambient temperature for 30 minutes and diluted with ethyl acetate. Several grams of MgSO4 were added, and the mixture was filtered through Celite diatomaceous filter aid and concentrated under reduced pressure to give 4.0 g of the title compound as a colorless oil. 1HNMR (CDCl3) δ 1.17 (s, 1H), 1.65-2.0 (m, 4H), 2.47 (s, 3H), 2.65-2.85 (m, 2H), 3.63 (m, 1H), 7.0-7.35 (m, 4H).
  • 6
  • [ 23357-46-2 ]
  • [ 407-25-0 ]
  • [ 1019207-94-3 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; In dichloromethane; at 0 - 20℃; (R)-2,2,2-Trifluoro-N-(l,2,3,4-tetrahydronaphthalen-l- yl)acetamide. A 250 ml round bottom flask was charged with of (R)- 1,2,3, 4- tetrahydronaphthalen-1 -amine (5 g, 34 mM), then purged with argon when DCM (50 ml) was added, and the solution was cooled to 0 0C. Triethylamine (9.5 mL) was added by syringe followed be trifluoroacetic anhydride (7.1 mL) of was added over 5 min by syringe. The solution was then stirred overnight, slowly warming to room temp. The mixture was diluted with DCM and washed with water, 1 N HCl, and brine. The organic layer was dried over MgSO4 and concentrated in vacuo, and purified by column chromatography (eluting with 1:1 DCM/Hex), to give 6.6g (80%) of the titled compound. IH-NMR (300 MHz, CDC13) δ 7.2 (m, 3H), 7.1 (t,lH), 6.5 (broad s, IH), 5.2 (q, IH), 2.8 (q, 2H), 2.1 (m IH), 1.9 (m, 3H) ppm.
With triethylamine; In dichloromethane; at 0 - 20℃; (R)-2,2,2-trifluoro-N-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide.; A 250 ml round bottom flask was charged with 5 g (34 mmol) of (R)-1,2,3,4-tetrahydronaphthalen-1-amine (Alfa Aesar). The flask was then purged with argon. 50 ml of DCM was then added, and the solution was cooled to 0 C. 9.48 ml (68 mmol) of TEA was added by syringe, then 7.09 ml (51 mmol) of trifluoroacetic anhydride was added slowly by syringe. The solution was then stirred overnight, slowly warming to room temp. The mixture was diluted with DCM and washed with water, 1 N HCl, and brine. The organic layer was dried over MgSO4 and concentrated in vacuo, and purified by column chromatography (eluting with 1:1 DCM:Hex), to give 6.63 g (80%) of the titled compound. 1H-NMR (CDCl3) δ 7.2 (m, 3H), 7.1 (t, 1H), 6.5 (br s, 1H), 5.2 (q, 1H), 2.8 (q, 2H), 2.1 (m 1H), 1.9 (m, 3H) ppm.
  • 7
  • [ 17153-20-7 ]
  • [ 23357-46-2 ]
  • (R)-3-methyl-isoxazole-4-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.5% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); dichloromethane; at 0 - 20℃; To a solution of 3-Methyl-isoxazole-4-carboxylic acid (0.52 g, 4.06 mmol) in DCM (15 mL) and DMF (2 mL), was added HOBt (1.1 g, 8.14 mmol) and EDCI (0.896 g 4.67 mmol). The clear yellow solution was cooled to 0 C and allowed to stir under Ar for 15 minutes. To the solution was added (R)-1-Amino-1,2,3,4-tetrahydronaphthalene (0.73 mL, 5.04 mmol and the reaction mixture was allowed to slowly warm to ambient temperature and was stirred for overnight. Dilution with DCM (50 mL) was followed by aqueous extraction (NaHCO3 water, brine (50 mL), drying over MgSO4, filtration and removal of solvent in vacuo. Silica gel chromatography (0-25% Hexane:EtOAc) afforded the title compound (650 mg; 62.5%) as a sticky solid. 1H NMR (CDCl3) δ 1.88 (m, 3H), 2.12 (m, 1H), 2.51 (s, 3H), 2.81 (m, 2H), 5.32 (m, 1H), 5.99 (bd, 1H), 7.13 (m, 1H), 7.20 (m, 2H) 7.20 (m, 2H); 13C NMR (CDCl3) δ 11.22, 20.15, 29.41, 30.35, 47.93, 116.73, 126.72, 127.88, 128.88, 129.65, 136.25, 138.00, 158.45, 160.28. ESIMS: 257 (M+H) EA calc'd for C15H16N2O2: C, 70.29; H, 6.29; N, 10.93; found C, 70.61; H, 6.11; N, 11.09.
  • 8
  • [ 488-93-7 ]
  • [ 23357-46-2 ]
  • (R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)furan-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); dichloromethane; at 0 - 20℃; for 24h; To a solution of furan-3-carboxylic acid (100 mg, 0.68 mmol), HOBt (240 mg, 1.78 mmol) and EDCI.HCl (196 mg, 1.03 mmol) in CH2Cl2 (8 mL) and DMF (1.5 mL) at 0 C., was added (R)-1,2,3,4-tetrahydronaphthalen-1-amine (160 μL, 1.06 mmol). The reaction was stirred at rt for 24 h, after which CH2Cl2 was added. The resulting solution was washed with saturated NaHCO3, H2O, brine, dried over MgSO4 and concentrated in vacuo. Recrystallization from EtOH/H2O afforded (R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-2,5-dihydrofuran-3-carboxamide. 1H NMR (500 MHz, CDCl3): δ 1.89 (m, 3H), 2.12 (m, 1H), 2.84 (m, 2H), 5.35 (m, 1H), 5.96 (br d, 1H, J=7.75 Hz), 6.59 (dd, 1H, J=1.90, 0.86 Hz), 7.13 (m, 1H), 7.19 (m, 2H), 7.32 (m, 1H), 7.43 (t, 1H, J=1.73 Hz), 7.93 (m, 1H). MS(M+H, 242).
  • 9
  • [ 23357-46-2 ]
  • [ 88-95-9 ]
  • [ 911826-62-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 0 - 70℃; (i?)-2-(l,2,3,4-Tetrahydronaphthalen-l-yl)isoindoline-l,3-dione. To a solution of (i?)-l,2,3,4-tetrahydro-l-naphthylamine (6.0 g) in THF (150 mL) at 0 0C was added TEA (18.5 mL) and phthaloyl chloride (8.2 g), and the resultant mixture was stirred at room temperature overnight and 70 0C for 3 h. The mixture was diluted with CH2Cl2, washed with saturated NaHCO3, dried over MgSO4, and concentrated in vacuo. The resulting crude was chromatographed on silica gel (EtOAc/hexane, 5/95 to 30/70) to afford 8.2 g of the title compound.
  • 10
  • [ 23357-46-2 ]
  • [ 913359-59-8 ]
YieldReaction ConditionsOperation in experiment
87% 4-Benzyl 1-tert-butyl (2S)-2-[(1 R)-1 ,2,3,4-tetrahydro-1-naphthalenyl- amino]carbonyl}-1 ,4-piperazinedicarboxylate (2);(2S)-4-[(benzyloxy)carbonyl]-1-(teAf-butoxycarbonyl)-2-piperazinecarboxylic acid (1, 17.33 g, 47.5 mmol) is dissolved in DMF (800 mL), to which is added diisopropylethylamine (DlEA, 41.5 mL, 0.24 mol). This mixture is stirred at RT for 1.5 h. R- f-j-1 ,2,3,4-tetrahydro-1-naphthylamine (7.00 g, 47.5 mmol) is added, and stirring continued for a further hour. O-(Benzotriazol-1-yl)-Λ/,/V,Λ/' /V-tetramethyluronium hexafluorophosphate (HBTU, 19.84 g, 52.3 mmol) and 1-hydroxybenzotriazole hydrate (HOBt, 7.07 g, 52.3 mmol) are also added and the entire mixture stirred overnight at RT. The reaction mixture is then diluted with EtOAc (1.2 L) and washed sequentially with 1 M citric acid, brine, sat. NaHCO3, brine, water and brine (1 L of each solution). The EtOAc layer is then dried with Na2SO4, filtered, and the solvent removed under reduced pressure to afford a crude off- white solid (23.34 g). This material is purified by flash chromatography on silica gel (CH2CI2 as eluent initially, followed by 5% Et2O/CH2CI2 to elute the desired product). The desired coupled product 6 is isolated as a white foam (20.37 g, 87% yield): 1H NMR δ (CDCI3) 7.27- 7.42 (m, 5 H), 7.06-7.19 (m, 4 H), 6.10 (br s, 1 H), 5.11-5.25 (br m, 3 H), 4.46-4.75 (br m, 2 H), 3.77-4.02 (br m, 2 H), 3.00-3.31 (br m, 3 H), 2.68-2.84 (m, 2 H), 1.97-2.07 (br m, 1 H), 1.69-1.84 (br m, 3 H), 1.43 (s, 9 H). LCMS (APCI+) 494.8 (MH+), 438.5 (MH+-tBu), 394.4 (MH+-BOC).
  • 11
  • [ 23357-46-2 ]
  • [ 913359-75-8 ]
YieldReaction ConditionsOperation in experiment
93% (S)-4-Benzyl-2-[(R)-(1 ,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyrj- piperazine-1-carboxylic acid tert-butyl ester (6): Anhydrous DMF ( 20 ml) is added to a 100 ml round bottom flask containing compound 4 ( 325 mg, 1.014 mmol) under N2. After ten minutes diisopropylamine ( 0.88 ml, 5.07 mmol) is added to the flask. It is then stirred at room temperature for 1.5 hrs. (R)- 1 ,2,3,4-Tetrahydro-1-napthylamine ( 149.3 mg, 1.014 mmol) is then added to the flask and stirred for 1 hr. HBTU ( 423.07 mg, 1.115 mmol) is added to the reaction followed by HOBT ( 152.1 mg, 1.126 mmol). The reaction mixture is then stirred at room temperature under N2 overnight at which point LCMS shows completion of the reaction. It is then diluted with EtOAc and washed subsequently with 1.0 M citric acid, brine, saturated sodiumbicarbonate, brine, water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound is flash column purified using hexane and ethylacetate gradient solvent system to yield 423 mg ( 93%) of the desired product 6. HPLC shows this compound to be greater than 99% pure.
  • 12
  • [ 23357-46-2 ]
  • [ 876623-95-9 ]
YieldReaction ConditionsOperation in experiment
Boc-L-proline (9.36 g, 43.5 mmol), HOBt (8.0 g, 52.2 mmol), EDC (10 g, 52.2 mmol) and DIPEA (30 mL, 174 mmol) were dissolved in dry dichloromethane (200 mL) under N2 and stirred for 10 min at room temperature. 1,2,3,4-R-Tetrahydronaphtylamine (6.72 g, 45.6 mmol) was then added and the solution was left to stir for 24 h at RT. The contents were then added to a separatory funnel along with EtOAc and washed with 10% citric acid (2×), saturated NaHCO3 (2×) and brine. The organic layer was collected, dried and concentrated under reduced pressure to provide 6-1a.
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