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[ CAS No. 91-21-4 ] {[proInfo.proName]}

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Chemical Structure| 91-21-4
Chemical Structure| 91-21-4
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Product Citations

Product Citations

Zhao, Spencer ; Loh, Kang Yong ; Tyson, Jonathan , et al. DOI:

Abstract: Catalytic reactions of a broad range of abiotic molecules and macromolecules are beyond the native capabilities of mammals. Natural enzymes from prokaryotes or plant-based eukaryotes have limited substrate scopes. Therefore, broadening the range of catalytic bond-forming reactions that function in physiological conditions would enable the syntheses of a vast array of molecules directly within biological systems. This approach may provide an alternative way to modulate cellular behaviors if such molecules can be synthesized with spatiotemporal control on specific cell types in living systems; furthermore, restricting synthesis to well-defined cells or cell-types would enable a potentially transformative approach of treating cells as separable reaction vessels within living organisms. Herein, we use genetic targeting to incorporate an organic photocatalytic dye onto specific cell types to enable in-situ light-controlled and spatially defined chemical synthesis of non-natural molecules. We demonstrate, for the first time, a photo-patterned organic coupling reaction in the extracellular matrix of living cells under dilute, aqueous, aerobic physiological conditions. A 6-fold contrast in reaction yield can be achieved between two adjacent HEK293FT cells with and without light exposure. The above photocatalysis can be initiated using mild confocal laser stimulation as low as 16 μW/mm2 at multiple wavelengths. Furthermore, the cell-type specific photocatalyzed C-H functionalization coupling reactions taking place on cell surfaces are used to demonstrate anabolic construction of non-natural products. The above findings lay an important foundation for developing future abiotic cell-type specific chemical syntheses in living organisms.

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Product Details of [ 91-21-4 ]

CAS No. :91-21-4 MDL No. :MFCD00006896
Formula : C9H11N Boiling Point : -
Linear Structure Formula :- InChI Key :UWYZHKAOTLEWKK-UHFFFAOYSA-N
M.W : 133.19 Pubchem ID :7046
Synonyms :

Calculated chemistry of [ 91-21-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.78
TPSA : 12.03 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 1.57
Log Po/w (WLOGP) : 0.8
Log Po/w (MLOGP) : 1.8
Log Po/w (SILICOS-IT) : 2.52
Consensus Log Po/w : 1.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.06 mg/ml ; 0.00796 mol/l
Class : Soluble
Log S (Ali) : -1.43
Solubility : 4.91 mg/ml ; 0.0369 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.0759 mg/ml ; 0.00057 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 91-21-4 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P260-P262-P264-P270-P271-P273-P280-P301+P310+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P308+P311-P361+P364-P405-P501 UN#:2922
Hazard Statements:H301-H310-H314-H332-H371-H412 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 91-21-4 ]

* 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 [ 91-21-4 ]

[ 91-21-4 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 91-21-4 ]
  • [ 75-03-6 ]
  • [ 25939-81-5 ]
  • 2
  • [ 91-21-4 ]
  • [ 107819-90-9 ]
  • [ 507228-45-7 ]
  • 3
  • [ 91-21-4 ]
  • [ 66491-03-0 ]
  • 4
  • [ 91-21-4 ]
  • [ 25939-81-5 ]
  • 5
  • [ 91-21-4 ]
  • [ 23687-26-5 ]
  • 6
  • [ 91-21-4 ]
  • [ 68500-37-8 ]
  • 4-(3,4-dihydro-1H-isoquinolin-2-yl)-7-methoxy-quinoline [ No CAS ]
  • 7
  • [ 694-05-3 ]
  • [ 91-21-4 ]
  • [ 38521-46-9 ]
  • [ 61607-68-9 ]
  • [ 34803-66-2 ]
  • C23H19BrNO2Pol [ No CAS ]
  • [ 20980-22-7 ]
  • [ 40481-13-8 ]
  • [ 6325-91-3 ]
  • [ 38026-46-9 ]
  • [ 37052-78-1 ]
  • [ 2637-37-8 ]
  • [ 64415-07-2 ]
  • [ 57658-36-3 ]
  • [ 34272-64-5 ]
  • [ 29490-19-5 ]
  • [ 24854-43-1 ]
  • [ 2252-63-3 ]
  • [ 6670-13-9 ]
  • [ 131242-36-9 ]
  • [ 35071-17-1 ]
  • [ 13906-09-7 ]
  • [ 2349-58-8 ]
  • [ 6640-24-0 ]
  • [ 51639-48-6 ]
  • C28H27N2O2Pol [ No CAS ]
  • C27H22N3O2PolS [ No CAS ]
  • C26H23N4O2PolS [ No CAS ]
  • C26H22N3O2PolS2 [ No CAS ]
  • C28H24N3O2PolS [ No CAS ]
  • C32H25N2O2PolS [ No CAS ]
  • C29H23N2O4PolS [ No CAS ]
  • C28H29N6O2PolS [ No CAS ]
  • C32H29N2O2Pol [ No CAS ]
  • C26H22N5O4PolS [ No CAS ]
  • C32H31N4O2Pol [ No CAS ]
  • C31H30N5O2Pol [ No CAS ]
  • C31H26N3O3PolS [ No CAS ]
  • C31H24N3O3PolS [ No CAS ]
  • C29H25N2O4PolS2 [ No CAS ]
  • C33H31FN3O2Pol [ No CAS ]
  • C30H26N3O5PolS [ No CAS ]
  • C30H23N4O4PolS [ No CAS ]
  • C35H32N3O2Pol [ No CAS ]
  • C33H31ClN3O2Pol [ No CAS ]
  • C38H29N2O3PolS [ No CAS ]
  • C33H24F3N2O2PolS [ No CAS ]
  • C35H34N3O3Pol [ No CAS ]
  • C38H30N3O2PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 20h;Combinatorial reaction / High throughput screening (HTS); Each resin from Step 3 was distributed into 24 fritted syringes (Torvig, 50 mg each, 50 mumol), for a total of 96 syringes, and was swelled in NMP (1 mL) for 30 min. The solvent was removed by filtration. Twenty-four solutions of the building blocks listed below (10 mmol each) and DIBA (3.5 mL, 20 mmol) in NMP (10 mL) were prepared. 3 mL of the 24 solutions was added to the 24 syringes for each resin from Step 3, accordingly. The suspensions were then shaken for 20 h on a Titer Plate Shaker. The reaction mixture was filtered and washed 5 times with methylene chloride (5 mL), 3 times with THF (5 mL), 3 times THF/H2O (3/1 v/v, 5 mL), and 3 times with THF (5 mL). The resins were then dried overnight under vacuum.
  • 8
  • [ 694-05-3 ]
  • [ 91-21-4 ]
  • [ 38521-46-9 ]
  • [ 61607-68-9 ]
  • [ 34803-66-2 ]
  • C22H18BrN2O2Pol [ No CAS ]
  • [ 20980-22-7 ]
  • [ 40481-13-8 ]
  • [ 6325-91-3 ]
  • [ 38026-46-9 ]
  • [ 37052-78-1 ]
  • [ 2637-37-8 ]
  • [ 64415-07-2 ]
  • [ 57658-36-3 ]
  • [ 34272-64-5 ]
  • [ 29490-19-5 ]
  • [ 24854-43-1 ]
  • [ 2252-63-3 ]
  • [ 6670-13-9 ]
  • [ 131242-36-9 ]
  • [ 35071-17-1 ]
  • [ 13906-09-7 ]
  • [ 2349-58-8 ]
  • [ 6640-24-0 ]
  • [ 51639-48-6 ]
  • C27H26N3O2Pol [ No CAS ]
  • C26H21N4O2PolS [ No CAS ]
  • C25H22N5O2PolS [ No CAS ]
  • C25H21N4O2PolS2 [ No CAS ]
  • C27H23N4O2PolS [ No CAS ]
  • C31H24N3O2PolS [ No CAS ]
  • C28H22N3O4PolS [ No CAS ]
  • C27H28N7O2PolS [ No CAS ]
  • C31H28N3O2Pol [ No CAS ]
  • C25H21N6O4PolS [ No CAS ]
  • C31H30N5O2Pol [ No CAS ]
  • C30H25N4O3PolS [ No CAS ]
  • C30H29N6O2Pol [ No CAS ]
  • C30H23N4O3PolS [ No CAS ]
  • C32H30ClN4O2Pol [ No CAS ]
  • C29H22N5O4PolS [ No CAS ]
  • C28H24N3O4PolS2 [ No CAS ]
  • C29H25N4O5PolS [ No CAS ]
  • C32H30FN4O2Pol [ No CAS ]
  • C34H31N4O2Pol [ No CAS ]
  • C34H33N4O3Pol [ No CAS ]
  • C32H23F3N3O2PolS [ No CAS ]
  • C37H28N3O3PolS [ No CAS ]
  • C37H29N4O2PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 20h;Combinatorial reaction / High throughput screening (HTS); Each resin from Step 3 was distributed into 24 fritted syringes (Torvig, 50 mg each, 50 mumol), for a total of 96 syringes, and was swelled in NMP (1 mL) for 30 min. The solvent was removed by filtration. Twenty-four solutions of the building blocks listed below (10 mmol each) and DIBA (3.5 mL, 20 mmol) in NMP (10 mL) were prepared. 3 mL of the 24 solutions was added to the 24 syringes for each resin from Step 3, accordingly. The suspensions were then shaken for 20 h on a Titer Plate Shaker. The reaction mixture was filtered and washed 5 times with methylene chloride (5 mL), 3 times with THF (5 mL), 3 times THF/H2O (3/1 v/v, 5 mL), and 3 times with THF (5 mL). The resins were then dried overnight under vacuum.
  • 9
  • [ 91-21-4 ]
  • [ 34667-88-4 ]
  • C16H13N3O2 [ No CAS ]
  • 10
  • [ 91-21-4 ]
  • [ 129722-34-5 ]
  • 7-(4-(3,4-dihydroisoquinolin-2(1H)-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.5% With potassium carbonate; In acetonitrile; at 60 - 65℃;Inert atmosphere; General procedure: To a mixture of the corresponding secondary amines 4a?4k(0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) in anhydrousCH3CN (7 mL) were added the appropriate intermediates 10?13(0.5 mmol). The reaction mixture was warmed to 60?65 C andstirred for 6?10 h under an argon atmosphere. After complete reaction,the solvent was evaporated under reduced pressure. The residuewas dissolved in water (30 mL) and the mixture was extractedwith dichloromethane (20 mL 3). The combined organic phaseswere washed with saturated aqueous sodium chloride (30 mL),dried over sodium sulfate, and filtered. The solvent was evaporatedto dryness under reduced pressure. The residue was purified on asilica gel chromatography using mixtures of dichloromethane/acetone(30:1) as eluent to afford the corresponding 3,4-dihydro-2(1H)-quinoline-O-alkylamine derivatives TM1?TM31.
9% With triethylamine; In 1,4-dioxane; at 110℃; for 2h; To the dioxane solution was added triethylamine (39 mg, 0.75 mmol) and 1,2,3,4- tetrahydroisoquinoline (40 mg, 0.3 mmol). The mixture was heated to 110 °C and stirred for 2 h. The solvent was concentrated and the residue was purified by flash column chromatography on silica gel to give Compound 91 as a yellow solid (8 mg, 9percent yield). MS (ESI): m/z 351 [M+H]+. NMR (400 MHz, CDC13): delta 8.26 (s, 1H), 7.11 (m, 3H), 7.02 (m, 2H), 6.52 (dd, J= 8.0 Hz, 1H), 6.33 (d, J= 2.0 Hz, lH), 4.97 (t, J= 6.0 Hz, 2H), 3.65 (s, 2H), 2.90 (m, 4H), 2.75 (t, J= 6.0 Hz, 2H), 2.58 (m, 4H), 1.83 (m, 2H), 1.78 (m, 2H).
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