606488-94-2|3-Hydroxycyclohexanecarboxylic acid| Ambeed

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Quality Control of [ 606488-94-2 ] Purity: 95% SDS Specification

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Product Details of [ 606488-94-2 ]

CAS No. :	606488-94-2
Formula :	C₇H₁₂O₃
M.W :	144.17
SMILES Code :	O=C(C1CC(O)CCC1)O
MDL No. :	MFCD19228828
InChI Key :	JBZDHFKPEDWWJC-UHFFFAOYSA-N
Pubchem ID :	5255726

Safety of [ 606488-94-2 ]

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

Computational Chemistry of [ 606488-94-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.86
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	36.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	57.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.09
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	0.34
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.62
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.	0.35
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	0.42
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.57

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.88
Solubility	18.9 mg/ml ; 0.131 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.11
Solubility	11.1 mg/ml ; 0.0772 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	0.14
Solubility	199.0 mg/ml ; 1.38 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	No
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	No
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.	-6.94 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.	0.56

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	0.0 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)	2.5

Application In Synthesis of [ 606488-94-2 ]

* 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 [ 606488-94-2 ]

[ 606488-94-2 ] Synthesis Path-Downstream 1~38

1
[ 67-56-1 ]
[ 606488-94-2 ]
[ 37722-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 70℃; for 16h;	10534] Step 1; To a solution of 3-hydroxycyclohexanecar- boxylic acid (1.25 g, 8.67 mmol) in MeOR (20 mE) at RT was added thionyl chloride (1.26 mE, 17.34 mmol). The resulting mixture was at 70 C. for 16 h. The reaction was cooled to RT, evaporated, and sequentially co-evaporated once with MeOR and twice with EtOAc to afford pure methyl 3-hydroxycyclo- hexanecarboxylate.

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 2218 - 2227.
[2]Patent: US2016/151375,2016,A1 .Location in patent: Paragraph 0534.

2
[ 67-56-1 ]
[ 606488-94-2 ]
[ 6125-56-0 ]
[ 6125-56-0 ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2401 - 2423.

3
[ 71-41-0 ]
[ 606488-94-2 ]
(+/-)-pentyl trans-3-hydroxycyclohexanecarboxylate [ No CAS ]
(+/-)-pentyl cis-3-hydroxycyclohexanecarboxylate [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2401 - 2423.

4
[ 606488-94-2 ]
[ 76140-18-6 ]

References: [1]Journal of the American Chemical Society,1980,vol. 102,p. 6736 - 6744.

5
[ 606488-94-2 ]
[ 4350-83-8 ]

References: [1]Canadian Journal of Chemistry,1993,vol. 71,p. 578 - 610.

6
[ 99-06-9 ]
[ 606488-94-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; acetic acid;rhodium; In ethyl acetate; at 80℃; under 5171.62 Torr; for 18h;	(lRS SR)-3-(^ (lZ)~2-tert-bntv 2~met YA-oxidoA 5'diazmA-- ylidene]amino}oxy)cyclohexanecarboxylic acidStep A: 3-hydroxycyclohexanecarboxylic acid; A solution of 3-hydroxybeitzoic acid (20.0 g, 145 rrrmol) in 600 mL EtOAc containing acetic acid (10.49 g, 175 mmol) and rhodium (3.0 g, 1.46 mmol) was put on hydrogenation apparatus at 100 psi and 80 C for 18 hours. After the catalyst was removed by filtration, the filtrate was concentrated down to afford the title compound.
11 g	With hydrogen; sodium hydroxide; In water; at 150℃; under 45603.1 Torr;	A I L pressure tank reactor (60 atm) containing a solution of 3-hydroxybenzoic acid (30 g, 217.20 mmol, 1.00 equiv), Raney Ni (5 g) and sodium hydroxide (6.4 g, 160.00 mmol, 0.74 equiv) in water (500 mL) was introduced H2 (gas, 60 atm) and the resulting solution was stirred overnight at 150C. After completion of the reaction, the reaction temperature was cooled down to room temperature and the solids were filtered out by filtration. The resulting solution was neutralized with 12 M HCl, extracted with 6 x 100 mL of tetrahydrofuran. The combined organic layers were dried over sodium sulfate and concentrated under vacuum to provide 3- hydroxycyclohexane-l-carboxylic acid (11 g, crude) as a white solid.
	With hydrogen; sodium hydroxide; In water; at 150℃;	[00354] Synthesis of compound 30.2. Into a 1 L pressure tank reactor (60 atm) containing a solution of 3-hydroxybenzoic acid (30 g, 217.20 mmol, 1.00 equiv), Raney Ni (5 g) and sodium hydroxide (6.4 g, 160.00 mmol, 0.74 equiv) in water (500 mL) was introduced H2 (gas, 60 atm) and the resulting solution was stirred overnight at 150C. After completion of the reaction, the reaction temperature was cooled down to room temperature and the solids were filtered out by filtration. The resulting solution was neutralized with 12 M HC1, extracted with 6 x 100 mL of tetrahydrofuran. The combined organic layers were dried over sodium sulfate and concentrated under vacuum to provide 30.2 (11 g, crude) as a white solid.

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 2218 - 2227.
[2]Canadian Journal of Chemistry,1993,vol. 71,p. 578 - 610.
[3]Patent: WO2011/146371,2011,A1 .Location in patent: Page/Page column 23.
[4]Patent: WO2014/11902,2014,A1 .Location in patent: Paragraph 00280-00281.
[5]Patent: WO2014/194242,2014,A2 .Location in patent: Paragraph 00353-00354.

7
[ 606488-94-2 ]
[ 67-63-0 ]
(±)-isopropyl cis-3-hydroxycyclohexane-1-carboxylate [ No CAS ]
(±)-isopropyl cis-3-hydroxy cyclohexane-1-carboxylate [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2401 - 2423.

8
[ 606488-94-2 ]
7,7-d2-6-Oxabicyclo<3.2.1>octane [ No CAS ]

References: [1]Canadian Journal of Chemistry,1993,vol. 71,p. 578 - 610.

9
[ 606488-94-2 ]
cis-Hydroxycyclohexyl-1,1-dideuteromethanol [ No CAS ]

References: [1]Canadian Journal of Chemistry,1993,vol. 71,p. 578 - 610.

10
[ 606488-94-2 ]
[ 21531-47-5 ]