62638-06-6|Dimethyl cyclohexane-1,3-dicarboxylate| Ambeed

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Quality Control of [ 62638-06-6 ] Purity: 95% SDS Specification

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Product Details of [ 62638-06-6 ]

CAS No. :	62638-06-6
Formula :	C₁₀H₁₆O₄
M.W :	200.23
SMILES Code :	O=C(C1CC(C(OC)=O)CCC1)OC
MDL No. :	MFCD07779254
InChI Key :	BZUOYGUOKMUSPA-UHFFFAOYSA-N
Pubchem ID :	138896

Safety of [ 62638-06-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 62638-06-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	0
Fraction Csp3	0.8
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	50.64
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.52
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	1.33
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.14
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.	1.16
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	1.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.49

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.66
Solubility	4.43 mg/ml ; 0.0221 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.	-2.04
Solubility	1.84 mg/ml ; 0.00921 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-1.24
Solubility	11.4 mg/ml ; 0.057 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	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.	-6.58 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	0.0
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)	2.75

Application In Synthesis of [ 62638-06-6 ]

* 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 [ 62638-06-6 ]

[ 62638-06-6 ] Synthesis Path-Downstream 1~36

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[ 14064-13-2 ]
[ 116152-18-2 ]

References: [1]Patent: US2889354,1955, .

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[ 141-43-5 ]
[ 100384-67-6 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 5185,5191.

3
[ 67-56-1 ]
[ 121-91-5 ]
[ 62638-06-6 ]

References: [1]Journal of Organic Chemistry,1971,vol. 36,p. 924 - 928.

4
[ 186581-53-3 ]
[ 108162-40-9 ]
[ 62638-06-6 ]

References: [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 2007 - 2012.

5
[ 186581-53-3 ]
[ 2495-35-4 ]
[ 2409-87-2 ]
[ 4336-20-3 ]
[ 62638-06-6 ]

References: [1]Canadian Journal of Chemistry,1980,vol. 58,p. 1144 - 1150.

6
[ 67-56-1 ]
[ 27768-32-7 ]
[ 62638-06-6 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 3006 - 3007.

7
[ 75-11-6 ]
[ 62638-06-6 ]
[ 75328-53-9 ]

Yield	Reaction Conditions	Operation in experiment
68%		EXAMPLE 28; l,3-Dicarbomethoxybicyclo[3.1.1]heptane; A cooled (-67C) solution of dry diisopropylamine (3.65mL, 26 mmol) in anhydrous THF (20mL) under nitrogen was treated via syringe with 2.5N n-butyllithiurn/hexane (9.6mL, 24 mmol), warmed to 0C for 5 min, then recooled (-67C). DMPU (12.1mL, 100 mmol) was added dropwise via addition funnel so as to keep pot temp < -60 C, then a solution of dimethylcyclohexane-l,3-dicarboxylate (4.00g, 20 mmol) in anhydrous THF (lOmL) was likewise added dropwise. After lh at -67C, diiodomethane (7.23g, 27 mmol) in THF (lOmL) was added dropwise, then the mixture was warmed to room temperature over lh stirred lh, cooled on an ice bath, and quenched with saturated aqueous ammonium chloride (20mL). The organic solvents were removed in vacuo and water (30mL) was added, and the aqueous was extracted with hexane (lOOmL, then 2X5 OmL). The combined organic extracts were washed with water (75mL), dried (MgSCU), and concentrated in vacuo, then dissolved in methylene chloride and passed through a pad of alumina in a fritted (3 OmL) funnel. The concentrated filtrate was chromatographed on silica gel (~200cc, eluted with 1:1 hexane/methylene chloride) to afford 4.65g (68%) of l-iodomethyl-l,3-dicarbomethoxycyclohexane as a colorless oil.The above intermediate (4.59g, 13.5 mmol) and DMPU (7.25mL, 60mmol) in anhydrous THF (30mL) under nitrogen was cooled to -67 C. Meanwhile, a cooled (-67 C) solution of dry diisopropylamine (2.6mL, 18 mmol) in anhydrous THF (2OmL) under nitrogen was treated via syringe with 2.4N n-butyllithium/~hexane (6.25mL, 15 mmol), warmed to 0 C for 5 minutes, and recooled (-67 C). The LDA solution was transferred via cannula in portions into the other solution at a rate to keep the pot temperature <-60 C, and the combined solution was stirred at -67 C for 30 minutes, warmed to room temperature over 75 minutes, and stirred 4h at room temperature. The mixture was cooled on an ice bath and quenched with saturated aqueous ammonium chloride (20mL), then partially concentrated in vacuo to remove organics and extracted with hexane (3X50mL). The combined extracts were washed with water (50mL), dried (MgSCU), and concentrated in vacuo, dissolved in methylene chloride and filtered through a pad of alumina in a 30 mL fritted glass funnel. The concentrated filtrate was chromatographed on silica gel (~120cc, eluted with 10% ethyl acetate/hexane) to afford 1.97g (69%) of subject material as a colorless oil. [M+H]+=213.2. *H NMR (CDC13) 5 3.66 (s, 6H), 2.45-2.55 (m, 2H), 1.75-2.00 (m, 8H).
68%		A cooled (-67C) solution of dry diisopropylamine (3.65mL, 26 mmol) in anhydrous THF (20mL) under nitrogen was treated via syringe with 2.5N n-butyllithium/hexane (9.6mL, 24 mmol), warmed to 0C for 5 min, then recooled (-67C). DMPU (12.1mL, 100 mmol) was added dropwise via addition funnel so as to keep pot temp < -60 C, then a solution of dimethyl cyclohexane-l,3-dicarboxylate (4.00g, 20 mmol) in anhydrous THF (lOmL) was likewise added dropwise. After Ih at -67C, diiodomethane (7.23g, 27 mmol) in THF (lOmL) was added dropwise, then the mixture was warmed to room temperature over Ih stirred Ih, cooled on an ice bath, and quenched with saturated aqueous ammonium chloride (20mL). The organic solvents were removed in vacua and water (30mL) was added, and the aqueous was extracted with hexane (lOOmL, then 2X5 OmL). The combined organic extracts were washed with water (75mL), dried (MgSO4), and concentrated in vacua, then dissolved in methylene chloride and passed through a pad of alumina in a fritted (30mL) funnel. The concentrated filtrate was chromatographed on silica gel (~200cc, eluted with 1:1 hexane/methylene chloride) to afford 4.65g (68%) of l-iodomethyl-l,3-dicarbomethoxycyclohexane as a colorless oil.The above intermediate (4.59g, 13.5 mmol) and DMPU (7.25mL, 60mmol) in anhydrous THF (30mL) under nitrogen was cooled to -67 C. Meanwhile, a cooled (-67 C) solution of drydiisopropylamine (2.6mL, 18 mmol) in anhydrous THF (20mL) under nitrogen was treated via syringe with 2.4N n-butyllithium/-hexane (6.25mL, 15 mmol), warmed to 0 C for 5 minutes, and recooled (-67 C). The LDA solution was transferred via cannula in portions into the other solution at a rate to keep the pot temperature <-60 C, and the combined solution was stirred at -67 C for 30 minutes, warmed to room temperature over 75 minutes, and stirred 4h at room temperature. The mixture was cooled on an ice bath and quenched with saturated aqueous ammonium chloride (20mL), then partially concentrated' in vacua to remove organics and extracted with hexane (3X50mL). The combined extracts were washed with water (50mL), dried (MgSO4), and concentrated in vacuo, dissolved in methylene chloride and filtered through a pad of alumina in a 30 mL fritted glass funnel. The concentrated filtrate was chromatographed on silica gel (~120cc, eluted with 10% ethyl acetate/hexane) to afford 1.97g (69%) of subject material as a colorless oil. .[M+H]+=213.2. 'H NMR (CDC13) 8 3.66 (s, 6H), 2.45-2.55 (m, 2H), 1.75-2.00 (m,8H).

References: [1]Patent: WO2006/12395,2006,A2 .Location in patent: Page/Page column 44-45.
[2]Patent: WO2006/12441,2006,A1 .Location in patent: Page/Page column 37-38.
[3]Journal of the American Chemical Society,1980,vol. 102,p. 6862.
[4]Journal of Organic Chemistry,1981,vol. 46,p. 4795 - 4797.

8
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References: [1]Australian Journal of Chemistry,1995,vol. 48,p. 967 - 986.
[2]Journal of the American Chemical Society,1980,vol. 102,p. 6862.
[3]Journal of the Chemical Society. Perkin transactions I,1999,p. 1725 - 1729.
[4]Australian Journal of Chemistry,1985,vol. 38,p. 1705 - 1718.
[5]Journal of the American Chemical Society,1991,vol. 113,p. 7969 - 7979.

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[ 3037-78-3 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 7969 - 7979.
[2]Tetrahedron Letters,2001,vol. 42,p. 4095 - 4097.

10
[ 62638-06-6 ]
[ 25090-39-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol;	To a solution of <strong>[62638-06-6]dimethyl 1,3-cyclohexanedicarboxylate</strong> (11.6 g, 57.9 mmol) in MeOH (58 mL) was added a 1N NaOH solution (58 mL) dropwise over 1 hr at 0 C. The resulting mixture was stirred at 0 C. for 0.5 hrs, and at room temperature for 2 hrs. The mixture was concentrated under reduced pressure, and the residual solution was partitioned between ethyl acetate and water. The aqueous phase was separated, acidified with conc. HCl (15 mL), saturated with NaCl, and then extracted with ethyl acetate. The extract was dried over Na2SO4, filtered and concentrated under reduced pressure to give 3-(methoxycarbonyl)cyclohexanecarboxylic acid as a colorless oil (6.16 g, yield; 57%).
	With sodium hydroxide; In methanol;	REFERENCE EXAMPLE 72 Monomethyl 1,3-cyclohexanedicarboxylate In 85 ml of methanol were dissolved 8.33 g of <strong>[62638-06-6]dimethyl 1,3-cyclohexanedicarboxylate</strong>, and 41.6 ml of 1N aqueous sodium hydroxide solution was added thereto, and the resulting mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure and the aqueous solution was washed with ethyl acetate. The pH was adjusted to 1 with diluted hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extracts were washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.7 g of the desired compound as a colorless oil. NMR spectrum (CDCl3) delta ppm: 1.20-2.45(9.3H,m), 2.65-2.80(0.7H,m), 3.68(3H,s)
	With sodium hydroxide; In methanol; at 0 - 20℃; for 2.83333h;	To a solution of dimethyl cyclohexane-1,3-dicarboxylat (2 g, 10 mmol) in MeOH (20 mL) was added a iN NaOH (10 mL) dropwise over 20 mm at 0 C. The resulting mixture was stirred at 0 C for 30 mm and RT for 2 hr. The mixture was concentrated under reduce pressure, and theresidue solution was partitioned between EA and water. The aqueous phase was separated,acidified with conc. HC1, saturate with NaC1, and then extracted with EA. The extract was dried over Na2SO4, filtered and concentrated to give the desired compound as colorless oil. ?H NMR (400 MHz, DMSO-d6) oe 12.12 (br s, 1H), 3.60 (s, 3H), 2.40-1.15 (m, 1OH).

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 4943 - 4950.
[2]Patent: US6562811,2003,B1 .
[3]Patent: US5843973,1998,A .
[4]Patent: WO2016/161960,2016,A1 .Location in patent: Paragraph 0543.

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[ 3971-28-6 ]
[ 62638-06-6 ]

References: [1]Canadian Journal of Chemistry,1980,vol. 58,p. 1144 - 1150.

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[ 62638-06-6 ]
[ 107-04-0 ]
[ 106004-11-9 ]
[ 106004-10-8 ]

References: [1]Australian Journal of Chemistry,1985,vol. 38,p. 1705 - 1718.

13
[ 62638-06-6 ]
[ 77-78-1 ]
[ 1142-41-2 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 3006 - 3007.

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[ 62638-06-6 ]
[ 74-88-4 ]
[ 1142-41-2 ]
dimethyl 1,3-dimethylcyclohexane trans-1,3-dicarboxylate [ No CAS ]
1-methyl-3-ethyl 1-methylcyclohexane cis-1,3-dicarboxylate [ No CAS ]
1-methyl-3-ethyl 1-methylcyclohexane trans-1,3-dicarboxylate [ No CAS ]

References: [1]Organic Mass Spectrometry,1994,vol. 29,p. 342 - 346.

15
[ 62638-06-6 ]
[ 74-95-3 ]
[ 75328-54-0 ]

References: [1]Australian Journal of Chemistry,1995,vol. 48,p. 967 - 986.

16
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[ 74-95-3 ]
dimethyl 1-bromomethylcyclohexane-1,3-dicarboxylate [ No CAS ]
dimethyl 1,3-di(bromomethyl)cyclohexane-1,3-dicarboxylate [ No CAS ]

References: [1]Australian Journal of Chemistry,1995,vol. 48,p. 967 - 986.

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[ 3971-28-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 1725 - 1729.
[2]Acta Crystallographica, Section C: Crystal Structure Communications,2013,vol. 69,p. 727 - 729.

Yield	Reaction Conditions	Operation in experiment
		Example 4 In a 300 ml pressure reactor, 10 g of the Ru catalyst were placed in a catalyst basket insert and 38.4 g (0.2 mol) of dimethyl isophthalate, dissolved in 100 g of THF, were added. The hydrogenation was carried out using pure hydrogen at 80 C. and a constant pressure of 200 bar. Hydrogenation was continued until no more hydrogen was taken up and the reactor was subsequently vented. The conversion of dimethyl isophthalate was 95.3%. The yield of dimethyl hexahydroisophthalate was 95.3%.

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