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Quality Control of [ 17754-90-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Citations

An eco-friendly and new facile method for synthesis of prenylated or geranylated acylphloroglucinol-based xanthenones

Raaginie Tamil Segaran ; Chean Hui Ng ; Mohd Fadhlizil Fasihi Mohd Aluwi , et al. Results Chem.,2024,101627. DOI: 10.1016j.rechem.2024.101627

Abstract: The synthesis of prenylated or geranylated acylphloroglucinol-based xanthenones with 15.1-36.9% yield was achieved via aldol condensation of 2,4,6-trihydroxy-3-prenylacetophenone (tHPA) or 2,4,6-trihydroxy-3-geranylacetophenone (tHGA) and 2-hydroxybenzaldehyde derivatives in the presence of lithium bis(trimethylsilyl)amide (LiHMDS) as deprotonating agent. This study is one of the first to report on the synthesis of xanthenones using strong non-nucleophilic base catalyst, and the described synthesis not only achieved a compound with a natural product skeleton but also formed in a simple and environmentally friendly specificity.

Keywords: Acylphloroglucinol-based xanthenone ; LiHMDS base catalyst ; Aldol condensation ; Natural product skeleton ; Eco-friendly

Purchased from AmBeed: 480-66-0 ; 18362-30-6 ; 17754-90-4

Product Details of [ 17754-90-4 ]

CAS No. :	17754-90-4	MDL No. :	MFCD00003326
Formula :	C₁₁H₁₅NO₂	Boiling Point :	No data available
Linear Structure Formula :	(OH)C₆H₃(CHO)N(C₂H₅)₂	InChI Key :	XFVZSRRZZNLWBW-UHFFFAOYSA-N
M.W :	193.24	Pubchem ID :	87293
Synonyms :

Calculated chemistry of [ 17754-90-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.67
TPSA :	40.54 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.8
Log Po/w (XLOGP3) :	1.75
Log Po/w (WLOGP) :	2.05
Log Po/w (MLOGP) :	1.42
Log Po/w (SILICOS-IT) :	1.8
Consensus Log Po/w :	1.76

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.19
Solubility :	1.24 mg/ml ; 0.0064 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	1.17 mg/ml ; 0.00605 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.69
Solubility :	0.39 mg/ml ; 0.00202 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 17754-90-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 17754-90-4 ]

* 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.

Upstream synthesis route of [ 17754-90-4 ]
Downstream synthetic route of [ 17754-90-4 ]

[ 17754-90-4 ] Synthesis Path-Upstream 1~2

1
[ 17754-90-4 ]
[ 74-88-4 ]
[ 55586-68-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: With potassium carbonate; potassium hydroxide In acetonitrile at 80℃; for 0.166667 h; Stage #2: at 80℃; for 2 h;	A mixture of 4-diethylamino-2-hydroxy benzaldehyde (5.8 g,30 mmol), KOH (2 g, 35 mol) and K2CO3 (8.3 g, 60 mmol) inacetonitrile (30 ml) was heated for 10 min at 80 °C. MeI (3.5 ml,56 mmol) was added to this alkaline mixture and stirring wascontinued for another 2 h at 80 °C. The reaction mixture was thencooled to room temperature filtered. The filtrate was concentratedunder reduced pressure and chromatographed on silica gel column(mesh sizee120-200) eluting with EtOAc/hexane in 1:3 ratio to get pure compound as yellow solid (yield 85percent).1H NMR (500 MHz, CDCl3) δ 10.11 (s, 1H), 7.68 (dd, J 8.9, 2.8 Hz,1H), 6.26 (d, J 8.8 Hz, 1H), 6.02 (s, 1H), 3.87 (s, 3H), 3.41 (dd,J 6.9, 2.7 Hz, 4H), 1.21 (t, J 5.4 Hz, 6H).13C NMR (125 MHz, CDCl3) δ: 187.1, 164.1, 153.8, 130.7, 114.2,104.2, 92.4, 55.2, 44.7, 12.5 (see Fig. 2).

Reference： [1] Journal of Physical Chemistry A, 2004, vol. 108, # 31, p. 6452 - 6454
[2] Dyes and Pigments, 2018, vol. 148, p. 474 - 491
[3] RSC Advances, 2013, vol. 3, # 46, p. 24021 - 24024
[4] Patent: US2017/320846, 2017, A1, . Location in patent: Sheet 16

2
[ 74-83-9 ]
[ 17754-90-4 ]
[ 55586-68-0 ]

Reference： [1] Dyes and Pigments, 2011, vol. 90, # 1, p. 56 - 64

[ 17754-90-4 ] Synthesis Path-Downstream 1~8

1
[ 17754-90-4 ]
[ 78364-55-3 ]
2-[2-(4-(N,N-diethylamino)-2-hydroxybenzylidene)hydrazino]-6-fluorobenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With acetic acid; In ethanol; at 80℃; for 0.166667h;Microwave irradiation;	General procedure: 2-(2-Arylidenehydrazino)-6-fluorobenzothiazoles 6a-r. General Procedure D. A mixture of compound 2 (0.0549 g, 0.0003 mol), the appropriate aromatic aldehyde (0.00033 mol) and glacial acetic acid (0.1 mL) in ethanol (5 mL) was heated under microwave (20 W) at 80 °C for 10 min. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized from the appropriate solvent to give the desired compounds 6a-r.

Reference： [1]Chinese Chemical Letters,2015,vol. 26,p. 1522 - 1528

2
[ 17754-90-4 ]
[ 98-32-8 ]
[ 105-56-6 ]
3-(5'-sulfonylamine-2'-benzoxazole)-7-diethylamino-2H-1-benzopyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In butan-1-ol; for 7h;Reflux;	General procedure: Salicylaldehyde (2 mmol), ethyl cyanoacetate (2 mmol), and o-aminophenol(2 mmol) were mixed in n-BuOH (20 mL), and the solution was refluxed for 7 h.The solvent was removed, and the residue was suspended in EtOH (10 mL) and stirred with 1 percent NaOH (10 mL) for 30 min. After filtration and washing with water,the product was obtained as yellow solid.

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 1017 - 1028

3
[ 17754-90-4 ]
[ 63655-40-3 ]
[ 1310062-98-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; for 12h;Reflux;	Benzimidazole based Schiff base 1 is prepared from 2-aminobenzimidazoleand aromatic aldehyde in absolute ethanolfor 12 h at reflux, as reported previously (17). Detailed description can be found in the Supporting Information.

Reference： [1]Supramolecular Chemistry,2018,vol. 30,p. 891 - 900

4
[ 17754-90-4 ]
[ 116668-47-4 ]
(E)-6-((4-(diethylamino)-2-hydroxybenzylidene)amino)-2-naphthoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With acetic acid; In ethanol; for 14h;	The synthetic route to (E)-6-((4-(diethylamino)-2-hydroxybenzylidene)amino)-2-naphthoic acid (DHNC), is illustrated in Scheme 1. This one-step reaction was performed under mild conditions,affording a yield of 58percent. The detailed synthetic procedures are described as follows. To an ethanol solution (120 mL) of <strong>[116668-47-4]6-amino-2-naphthoic acid</strong> (1 g, 5.34 mmol) was added 4-(diethylamino)-2-hydroxybenzaldehyde (1.03 g, 5.34mmol), followed by dropwise addition of acetic acid (0.1 mL). After stirring at 65 °C for 12 h, precipitates are formed. Then the reaction was cooled down to 0 °C and stirred for 2 h. The resulting precipitated solid was collected by vacuum filtration,rinsed with ethanol. Its structurewas characterized by 1H NMR (Fig. S1),13C NMR (Fig. S2) and HRMS spectra (Fig. S3) with satisfactory results.The relevant data are extracted from the original spectra and listedbelow. 1H NMR (600 MHz, DMSO?d6) of DHNC, delta (ppm): 13.59 (br1H), 12.97 (br, 1H), 8.85 (s, 1H), 8.56 (s, 1H), 8.12?8.11 (d, 1H),7.97?7.93 (q, 2H), 7.82 (d, 1H), 7.64?7.62 (dd, 1H), 7.37?7.35 (d, 1H),6.35?6.33 (dd, 1H), 6.08 (d, 1H), 3.41?3.37 (q, 4H), 1.12?1.10 (t, 6H).13C NMR (151 MHz, DMSO?d6) of DHNC, delta (ppm): 167.87, 163.99, 162.62, 152.28, 148.46, 136.43, 134.90, 131.09, 130.79, 130.70, 128.31,127.58, 126.20, 121.98, 118.09, 109.19, 104.55, 97.24, 44.40, 12.99.HRMS of CHM1: m/z 363.1721 [(M+ H)+], calcd 363.1709. (Abbreviation:s = singlet, d = doublet, t = riplet, m = multiplet, br= broad).

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2019,vol. 214,p. 348 - 354

5
[ 30616-38-7 ]
[ 17754-90-4 ]
2-(benzo[d]thiazol-2-yl)-4-((4-(diethylamino)-2-hydroxybenzylidene)amino)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid; In ethanol; at 20℃; for 8h;	General procedure: In a stirred mixture of 5-amino-2-(benzo[d]thiazol-2-yl) phenol(3a) or 4-amino-2-(benzo[d]thiazol-2-yl) phenol (3b)(1.0 mmol) and substituted salicylaldehyde (1.2m/m of 3aand 3b) in ethanol added few drops of acetic acid. The reactionmixture was stirred at room temperature for 8 h. Theprecipitate was filtered and recrystallized with hot ethanol.

Reference： [1]Journal of Biomolecular Structure and Dynamics,2020,vol. 38,p. 1772 - 1785

6
[ 30616-38-7 ]
[ 17754-90-4 ]
(E)-2-(benzo[d]thiazol-2-yl)-4-(4-(diethylamino)-2-hydroxybenzylideneamino)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In tetrahydrofuran; for 8h;Reflux;	HBT (100mg, 0.41mmol) was refluxed with 4-(diethylamino)-2-hydroxybenzaldehyde (79mg, 0.41mmol) in 10mL Tetrahydrofuran (THF) for 8h. Reaction mixture was concentrated on water bath and the product obtained was purified by column chromatography which yielded green solid of (E)-2-(benzo[d]thiazol-2-yl)-4-(4-(diethylamino)-2-hydroxybenzylideneamino)phenol (HBTA) (Scheme 1; X=S). Yield: 155mg, 87%. 1H NMR (SFig. 1b) delta in ppm: 13.79 (s, 1H), 13.38 (s, 1H), 9.85 (1s, 1H), 8.20 (d, 2H), 7.52-7.30 (m, 4H), 6.88 (d, 8.4Hz, 1H), 6.01 (dd, 0.8Hz, 2H), 3.559 (dd, H) LC-MS (SFig. 2b): Calc. for C20H15N3O2 [M+H+]: 420.2 Found: 420.2.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2019,vol. 382

7
[ 17754-90-4 ]
[ 7474-78-4 ]
2-(4-(diethylamino)-2-hydroxyphenyl)-1H-benzo[d]imidazole-5-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium metabisulfite; In ethanol; water; for 24h;Reflux;	General procedure: To a solution of the appropriate 3,4-diaminobenzene derivative (1ad)(2 mmol) in ethanol (15 mL) 2.85 N aqueous solution of sodium metabisulphite (1.6 mL) and the appropriate substituted arylaldehyde(2 mmol) were added. The reaction mixture was heated at reflux for 24 h. The solvent was then evaporated under reduced pressure. The residue was added with HCl 1 N (10 mL), the formed precipitate was filtered off, washed with water (3×10 mL) and purified by crystallization from the adequate solvent to give the title compounds.Following the general procedure benzimidazoles 3 [19], 4 [20], 5 [21],7 [24], 6, 32 and 33 [15] were prepared and their analytical and spectral data are in agreement with those reported in literature.

Reference： [1]Bioorganic Chemistry,2019

8
[ 17754-90-4 ]
[ 36997-31-6 ]
C₄₂H₅₁N₉O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In methanol; for 24.0h;Reflux;	General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN).

Reference： [1]Polyhedron,2020,vol. 186

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Technical Information

? Acidity of Phenols ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? Mannich Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 17754-90-4 ] {[proInfo.proName]}

Quality Control of [ 17754-90-4 ]

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[ 17754-90-4 ] Synthesis Path-Upstream 1~2

[ 17754-90-4 ] Synthesis Path-Downstream 1~8

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Aryls

Aldehydes

Amines

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[ 17754-90-4 ]