[ CAS No. 18448-47-0 ] {[proInfo.proName]}

Name: 18448-47-0|Methyl cyclohex-1-enecarboxylate|98%
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COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 18448-47-0 ]

Product Details of [ 18448-47-0 ]

CAS No. :	18448-47-0	MDL No. :	MFCD00001544
Formula :	C₈H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KXPWRCPEMHIZGU-UHFFFAOYSA-N
M.W :	140.18	Pubchem ID :	87647
Synonyms :

Calculated chemistry of [ 18448-47-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.62
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.27
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	2.03
Log Po/w (WLOGP) :	1.66
Log Po/w (MLOGP) :	1.46
Log Po/w (SILICOS-IT) :	1.78
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.86
Solubility :	1.95 mg/ml ; 0.0139 mol/l
Class :	Very soluble
Log S (Ali) :	-2.21
Solubility :	0.864 mg/ml ; 0.00617 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.35
Solubility :	6.3 mg/ml ; 0.045 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.41

Safety of [ 18448-47-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18448-47-0 ]

* 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 [ 18448-47-0 ]
Downstream synthetic route of [ 18448-47-0 ]

[ 18448-47-0 ] Synthesis Path-Upstream 1~5

1
[ 18448-47-0 ]
[ 54396-74-6 ]

Reference： [1] Journal of the American Chemical Society, 2004, vol. 126, # 42, p. 13622 - 13623
[2] Journal of Organic Chemistry, 1982, vol. 47, # 26, p. 5093 - 5096
[3] Chemistry - A European Journal, 2008, vol. 14, # 5, p. 1654 - 1665
[4] Green Chemistry, 2017, vol. 19, # 2, p. 511 - 518
[5] Angewandte Chemie - International Edition, 2007, vol. 46, # 7, p. 1097 - 1100
[6] Journal of Organometallic Chemistry, 2007, vol. 692, # 24, p. 5523 - 5527
[7] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4806 - 4809
[8] Tetrahedron Letters, 1988, vol. 29, # 51, p. 6779 - 6782
[9] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 11, p. 1285 - 1288
[10] Tetrahedron, 1995, vol. 51, # 43, p. 11751 - 11764
[11] Green Chemistry, 2017, vol. 19, # 21, p. 5122 - 5130

2
[ 18448-47-0 ]
[ 33668-25-6 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 21, p. 5122 - 5130

3
[ 18448-47-0 ]
[ 16205-98-4 ]

Reference： [1] Tetrahedron Letters, 1988, vol. 29, # 51, p. 6779 - 6782

4
[ 79368-45-9 ]
[ 149-73-5 ]
[ 18448-47-0 ]
[ 6493-77-2 ]
[ 3399-22-2 ]
[ 3399-21-1 ]
[ 79368-46-0 ]

Reference： [1] Liebigs Annalen der Chemie, 1981, # 8, p. 1394 - 1406

5
[ 18448-47-0 ]
[ 89490-05-1 ]

Reference： [1] Patent: CN104788481, 2016, B,

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Yield	Reaction Conditions	Operation in experiment
100%	With diisobutylaluminium hydride; In dichloromethane; toluene; at -78℃; for 1h;	Step 1: Cyclohex-l-en-l-ylmethanol To a solution of methyl 1-cyclohexene-l-carboxylate (1.50 mL, 11.0 mmol) in DCM (30 mL) was added diisobutylaluminum hydride (1M solution in toluene; 25 mL, 25 mmol) at -78 C and the mixture was stirred for 1 h. TLC (3:1 hex:EtOAc) showed that the reaction was then complete. The mixture was quenched with methanol (10 mL) and IN NaOH (10 mL) and then was allowed to stir at rt for 2.5 h. The mixture was extracted with DCM (3x). The combined organic layers were washed with brine, dried over MgSCt, filtered and concentrated to give cyclohex-l-en-l-ylmethanol (1.3 g, 100%).
99%	With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 2h;	To a solution of DIBAL (10.7 mmol) in dry dichloromethane (20 mL), cooled at -78 C, methylcyclohex-1-enecarboxylate (485 muL, 3.57 mmol) was added dropwise. The mixture was stirred for 2S5h at -78 C, then it was treated with methanol (500 muL) and a saturated solution of NH4Cl (10 mL).The resulting mixture was allowed to reach 25 C, filtered and extracted with dichloromethane (3 x20 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated.The crude material was purified by flash chromatography on silica gel (1:5 ethyl acetate/petroleumether), to give 14p as a dark yellow oil (99% yield). 1H NMR (300 MHz, CDCl3): delta 5.67 (s, 1H), 3.97 (s,2H), 2.00 (br s, 4H), 1.66 - 1.53 (m, 4H), 1.42 (br s, 1H).
92%	With C39H53ClN2P2Ru; potassium methanolate; hydrogen; In tetrahydrofuran; at 20℃; under 3800.26 Torr;Glovebox;	General procedure: In a glove box, add a ruthenium complex Il (0.75 mg, 0.001 mmol),Potassium methoxide (7 mg, 0.1 mmol), tetrahydrofuran (2 mL), and ester compound (1 mmol).After sealing the autoclave, take it out of the glove box and fill it with 5atm of hydrogen.The reaction vessel was stirred at room temperature for 16 to 24 hours.After slowly releasing excess hydrogen, the reaction solution was depressurized to remove the solvent, and the residue was purified by a short column of silica gel to obtain an alcohol compound.The results are shown in Table 9.

63%	With [Ru(2-(methylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate; hydrogen; In toluene; at 40 - 60℃; under 22502.3 Torr; for 6h;Autoclave;	Methyl cyclohex-1 -ene-1 -carboxylate was hydrogenated according to Example 18.The reaction mixture was initially heated to 60C. After stirring for 1 hour the vessel was allowed to cool down to 40C and was kept at this temperature under stirring for5 hours. Column chromatography yielded 0.75 g (63%) of cyclohex-1 -en-1 -ylmetha- nol.
	With diisobutylaluminium hydride; In tetrahydrofuran; at -78℃; for 4h;	To a stirred solution of methyl cyclohex-1-enecarboxylate (4.56 g, 32 mmol) in THF (100 mL) at -78 C. was added DIBAL (1 M in THF, 130 mmol, 130 mL) dropwise. The mixture was allowed to stir at -78 C. for 4 h then treated with a saturated NaHCO3 solution (40 mL). The aqueous layer was extracted with EtOAc (4×20 mL) and the combined organic layers were washed with H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4),and concentrated under reduced pressure. The residual cyclohex-1-enylmethanol was used directly for the next step without purification: TLC (30% EtOAc/hex) Rf0.44

Yield	Reaction Conditions	Operation in experiment
40%	With trifluoroacetic acid; In 1,2-dichloro-ethane; at 20℃; for 2h;	To a solution of <strong>[18448-47-0]methyl cyclohex-1-ene-1-carboxylate</strong> (19, 25.0 g, 178 mmol) andN-benzyl-N-methoxymethyl-N-trimethylsilylamine (46.6 g, 196 mmol) in 1,2-dichloroethane (178 mL)was added trifluoroacetic acid (0.14 mL, 1.78 mmol) at ambient temperature. After the reaction solutionwas stirred for 2 h, to the mixture were added saturated aqueous NaHCO3 and CHCl3. The organicsolution was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The resultantresidue was purified by silica gel column chromatography, eluting with hexane/EtOAc = 3:1 to yield 20(21.3 g, 40%) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 1.21-1.53 (6H, m), 1.65-1.79 (2H, m),1.90-1.96 (1H, m), 2.68-2.73 (3H, m), 2.92 (1H, d, J = 9.3 Hz), 3.65-3.70 (5H, m), 7.24-7.32 (5H, m).MS (ESI) m/z: 274 (M + H)+.
	trifluoroacetic acid; In 1,2-dichloro-ethane; at 20℃; for 2h;	[Reference Example 131]; [ (IR, 6R) -delta-Benzyl-S-azabicyclo [4.3.0] nonan-1- yl] carboxylic acid methyl ester; [Formula 227]COOMe (+/-) -cis A catalytic amount of trifluoroacetic acid was added to a solution of 1-cyclohexene-l-carboxylic acid methyl ester(25.0 g, 178 mmol) and N-benzyl-N- (methoxymethyl) -N- trimethylsilylmethylamine (46.6 g, 196 mmol) in 1,2- dichloroethane (178 mL) at room temperature, and the mixture was stirred at room temperature for two hours. A saturated sodium bicarbonate solution (200 mL) was added to the reaction solution, followed by extraction with chloroform (15O mL x I, lOO mL x l). The organic layer was washed with brine (450 ml) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated <n="364"/>under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane : ethyl acetate = 100:0 -> 90:10 -> 85:15 -> 75:25) to give 21.3 g of the title compound. 1H-NMR (400 MHz, CDCl3) delta: 7.32-7.24 (5H, m) , 3.70-3.65 (5H, m) , 2.92 (IH, d, J=9.31 Hz), 2.73-2.68 (3H, m) , 1.93 (IH, td, J=9.01, 4.82 Hz), 1.79-1.65 (2H, m) , 1.53-1.21 (6H, m) . MS (ESI); m/z: 274 (M+H)+.

Yield	Reaction Conditions	Operation in experiment
	With D-glucose; cytochrome P₄₅₀-BM₃mutant V₇₈L/A₈₂F/F₈₇A from Bacillus megaterium; NADPH Enzymatic reaction;
	Multi-step reaction with 2 steps 1: chromium(VI) oxide; acetic anhydride / acetic acid; dichloromethane / 0 - 5 °C 2: OYE₁ ene-reductase; D-glucose; nicotinamide adenine dinucleotide phosphate; glucose dehydrogenase from Bacillus megaterium / dimethyl sulfoxide / 24 h / 30 °C / Enzymatic reaction

[ CAS No. 18448-47-0 ] {[proInfo.proName]}

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