327183-32-4|Chroman-8-carbaldehyde| Ambeed

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Quality Control of [ 327183-32-4 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 327183-32-4 ]

CAS No. :	327183-32-4
Formula :	C₁₀H₁₀O₂
M.W :	162.19
SMILES Code :	O=CC1=CC=CC2=C1OCCC2
MDL No. :	MFCD12198125
InChI Key :	ZYKTXRDSAFQAAM-UHFFFAOYSA-N
Pubchem ID :	22265336

Safety of [ 327183-32-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 327183-32-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	45.98
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.99
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.82
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.35
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.96

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.25
Solubility	0.908 mg/ml ; 0.0056 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.92
Solubility	1.95 mg/ml ; 0.012 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.91
Solubility	0.201 mg/ml ; 0.00124 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.05 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.91

Application In Synthesis of [ 327183-32-4 ]

* 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 [ 327183-32-4 ]

[ 327183-32-4 ] Synthesis Path-Downstream 1~25

1
[ 1001671-65-3 ]
[ 68-12-2 ]
[ 327183-32-4 ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 10322 - 10325.
[2]Advanced Synthesis and Catalysis,2007,vol. 349,p. 193 - 203.

2
[ 327183-32-4 ]
[ 19493-09-5 ]
8-vinyl-3,4-dihydro-2H-1-benzopyran [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 193 - 203.

3
[ 608-33-3 ]
[ 327183-32-4 ]

References: [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 193 - 203.
[2]Chemistry - A European Journal,2015,vol. 21,p. 10322 - 10325.
[3]Patent: WO2008/82488,2008,A1 .

5
[ 493-08-3 ]
[ 327183-32-4 ]
8-chromanylacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With n-butyllithium; In tetrahydrofuran; N-methyl-acetamide;	8-Chromanylacetic acid can be prepared in three stages from chroman, with an overall yield of 60%, as illustrated by Synth. Comm., 12, 763-70 (1982). On treatment with n-butyllithium and then with dimethylformamide in tetrahydrofuran, chroman results in 8-chromanal, which is then treated with trimethylsilyl cyanide in the presence of zinc iodide in dichloromethane.

References: [1]Patent: US5936097,1999,A .

6
[ 67-56-1 ]
[ 637-81-0 ]
[ 327183-32-4 ]
[ 124-41-4 ]
C₁₃H₁₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	In tetrahydrofuran; at -20 - 5℃; for 5.5h;	Step C - Synthesis of Compound 21 D; To a solution of compound 21C (25.89 mmol) in 10 mL of methanol and 10 mL of THF at 0 0C was added a solution of ethyl azido acetate (10.0g, 77.69 mmol) in 10 mL of methanol. The reaction was cooled to -20 C, and a solution of freshly prepared sodium methoxide in methanol (prepared by dissolving 1.78 g sodium in 80 mL of methanol) was added dropwise (the internal temperature was kept below 5C). The reaction mixture was stirred at approximately 5 C for 0.5 hours, and then stirred at 0 C for 5 hours. The reaction was quenched with aqueous saturated ammonium chloride solution (20 mL), then ethyl acetate (400 mL) and water (80 mL) were added, and the layers separated. The organic layer was <n="147"/>washed with brine (80 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product obtained was purified on a Biotage 75-M column (gradient: 0 to 25% ethyl acetate in hexanes) to provide compound 21D (2.68 g, 41 %). 1H NMR (400 MHz, CDC13):5 8.00 (d, J= 8.1 Hz, IH), 7.35 (s, IH), 7.02 (d, J= 8.1 Hz, IH), 6.86 (t, J= 7.7 Hz, IH), 4.25 (t, J= 5.1 Hz, 2H), 3.81 (s, 3H), 2.79 (t, J= 6.2 Hz, 2H), 2.03 - 1.97 (m, 2H).

References: [1]Patent: WO2008/82488,2008,A1 .Location in patent: Page/Page column 143-145.

7
[ 68-12-2 ]
[ 206347-33-3 ]
[ 327183-32-4 ]

Yield	Reaction Conditions	Operation in experiment
88%		Step B - Synthesis of Compound 21 C; To a solution of compound 21B (10.9 g, 29.23 mmol) in dry THF (240 mL) and hexanes (40 mL) under anhydrous atmosphere at -78 0C, was added n-butyl lithium (20 mL of a 2.5M solution in toluene) dropwise. During the addition, the internal temperature of the solution was kept below 5 0C. The reaction mixture was stirred at approx. 5 C for 4 hours before a slow addition of additional n-butyl lithium (5.8 mL of a 2.5M solution in toluene diluted into 20 ml hexanes). The resulting mixture was stirred at 5 0C for 0.5 hours, followed by an addition of a solution of dimethyl formamide (3.38 mL, 43.84 mmol) in 10 mL of THF. The reaction mixture was stirred at 5 C for 10 minutes, then was warmed to room temperature and stirred for an additional 0.5 hours, and quenched with aqueous 1 N HCl solution (100 mL). The layers were separated, and the aqueous layer was extracted with ether (3 x 200 mL). The combined organic layers were washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography using a Biotage 75-M silica gel column (gradient: 0 to 20 % ethyl acetate in hexanes) to provide compound 21C (4.20 g, 88 %). 1H NMR (400 MHz, CDC13): delta 10.41 (s, IH), 7.64 & 7.63 (dd, J= 1.5 Hz, 8.1 Hz, IH), 7.25 (d, J= 5.13 Hz, IH), 6.89 (t, J= 7.3 Hz, IH), 4.30 (t, J= 5.1 Hz, 2H), 2.83 (t, J= 6.2 Hz, 2H), 2.09 - 2.03 (m, 2H).

References: [1]Patent: WO2008/82488,2008,A1 .Location in patent: Page/Page column 143-144.

8
[ 327183-32-4 ]
C₃₁H₃₆Cl₂N₂ORu [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 10322 - 10325.

9
[ 327183-32-4 ]
[ 1779-49-3 ]
8-vinyl-3,4-dihydro-2H-1-benzopyran [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 10322 - 10325.

10
[ 327183-32-4 ]
[ 75-64-9 ]
N-(chroman-8-ylmethylene)tert-butylamine [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372.

11
[ 327183-32-4 ]
6-(3-hydroxypropyl)biphenyl-2-carbaldehyde [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372.

12
[ 327183-32-4 ]
6-(3-hydroxypropyl)-4'-methylbiphenyl-2-carbaldehyde [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372.

13
[ 327183-32-4 ]
6-(3-hydroxypropyl)-4'-methoxybiphenyl-2-carbaldehyde [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372.

14
[ 327183-32-4 ]
4'-fluoro-6-(3-hydroxypropyl)biphenyl-2-carbaldehyde [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372.

15
[ 327183-32-4 ]
4'-chloro-6-(3-hydroxypropyl)biphenyl-2-carbaldehyde [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372.

16
[ 327183-32-4 ]
6-(3-hydroxypropyl)-4'-phenylbiphenyl-2-carbaldehyde [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 14367 - 14372.

17
[ 327183-32-4 ]
tert-butyl 6-benzyloxy-7-methoxy-1-[(1-phenyltetrazol-5-yl)sulfonylmethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate [ No CAS ]
6-benzyloxy-1-[(E)-2-chroman-8-ylvinyl]-7-methoxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of tert-Butyl 6-benzyloxy-7-methoxy-1-[(1-phenyltetrazol-5-yl)sulfonylmethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate (100 mg, 0.169 mmol) and <strong>[327183-32-4]chromane-8-carbaldehyde</strong> (136 mg, 0.84 mmol) in THF (10 mL) was cooled to -35 C. with stirring under argon. To this mixture was added a solution of lithium bis(trimethylsilyl)amide (0.68 mL, 0.68 mmol, 1M in THF) and the reaction mixture was stirred for 1 hour at -35 C. The reaction was allowed to warm up to room temperature and the organic solvent was evaporated to give a residue. The residue was dissolved (or suspended) in 4M HCl dioxane (5 mL) and stirred at room temperature until the reaction was completed. The organic layer was evaporated to leave a residue, which was purified by flash or reverse phase preparatory chromatography. LC-MS; M+1=428.

References: [1]Patent: US2016/168100,2016,A1 .Location in patent: Paragraph 0464-0465.

18
[ 327183-32-4 ]
C₁₄H₁₄O₃ [ No CAS ]