Cyclohexanecarboxylic acid, ethyl ester, cis-

Base Information

• Chemical Name: Cyclohexanecarboxylic acid, ethyl ester, cis-
• CAS No.: 3326-96-3
• Molecular Formula: C17H25NO6
• Molecular Weight: 339.3835
• NSC Number: 102724
• DSSTox Substance ID: DTXSID10954904
• Wikidata: Q82934342
• ChEMBL ID: CHEMBL3276031
• Mol file: 3326-96-3.mol

Synonyms:33073-61-9;CHEMBL3276031;DTXSID10954904;NSC102724;NSC-102724;Cyclohexanecarboxylic acid, ethyl ester, cis-;Cyclohexanecarboxylic acid, ethyl ester, (Z)-;N-(2-Chloroethyl)-N'-[3-(ethoxycarbonyl)cyclohexyl]-N-nitrosocarbamimidic acid

Chemical Property of Cyclohexanecarboxylic acid, ethyl ester, cis-

Chemical Property:

• Vapor Pressure: 2.03E-13mmHg at 25°C
• Boiling Point: 529.4°C at 760 mmHg
• Flash Point: 274°C
• Density: 1.24g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 305.1142338
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1CCCC(C1)NC(=O)N(CCCl)N=O
• Isomeric SMILES: CCOC(=O)[C@H]1CCC[C@H](C1)NC(=O)N(CCCl)N=O

Technology Process of Cyclohexanecarboxylic acid, ethyl ester, cis-

There total 12 articles about Cyclohexanecarboxylic acid, ethyl ester, cis- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

Acetic acid (1R,3S,5S)-3-[(R)-2-(2,6-dioxo-piperidin-4-yl)-1-triethylsilanyloxy-ethyl]-1,5-dimethyl-4-oxo-cyclohexyl ester (131057-04-0) → (+/-)-E-73 (2885-39-4,131102-35-7,14172-67-9,3326-96-3,11037-68-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1271/bbb1961.54.1531

Reference yield:

4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone (60739-53-9) → (+/-)-E-73 (2885-39-4,131102-35-7,14172-67-9,3326-96-3,11037-68-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / diethyl ether / 1 h / Ambient temperature

2: 61 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 - 70 °C

3: 88 percent / pyridinium chlorochromate (PCC), NaOAc / CH₂Cl₂ / 8 h / Ambient temperature

4: 84 percent / dimethylformamide / 80 °C

5: 1) lithium diisopropylamide / 1) THF, -60 deg C, 20 min, 2) -60 to -5 deg C

6: 1) lithium diisopropylamide / 1) THF, -70 deg C, 15 min, 2) -70 deg C, 1 h

7: 30 percent aq. acetic acid / tetrahydrofuran / 3 h / Ambient temperature

8: 71 percent / triethylamine, 4-dimethylaminopyridine / 48 h / Ambient temperature

9: 40 percent / triethylamine, 4-dimethylaminopyridine / 7 h / ice-NaCl bath

10: 70 percent / aq. acetic acid / tetrahydrofuran / 4 h / Ambient temperature

With dmap; sodium acetate; pyridinium p-toluenesulfonate; acetic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb1961.54.1531

Reference yield:

1-methyl-1,4-cyclohexanediol (89794-52-5) → (+/-)-E-73 (2885-39-4,131102-35-7,14172-67-9,3326-96-3,11037-68-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / pyridinium chlorochromate (PCC), NaOAc / CH₂Cl₂ / 8 h / Ambient temperature

2: 84 percent / dimethylformamide / 80 °C

3: 1) lithium diisopropylamide / 1) THF, -60 deg C, 20 min, 2) -60 to -5 deg C

4: 1) lithium diisopropylamide / 1) THF, -70 deg C, 15 min, 2) -70 deg C, 1 h

5: 30 percent aq. acetic acid / tetrahydrofuran / 3 h / Ambient temperature

6: 71 percent / triethylamine, 4-dimethylaminopyridine / 48 h / Ambient temperature

7: 40 percent / triethylamine, 4-dimethylaminopyridine / 7 h / ice-NaCl bath

8: 70 percent / aq. acetic acid / tetrahydrofuran / 4 h / Ambient temperature

With dmap; sodium acetate; acetic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb1961.54.1531

upstream raw materials:

Acetic acid (1R,3S,5S)-3-[(R)-2-(2,6-dioxo-piperidin-4-yl)-1-triethylsilanyloxy-ethyl]-1,5-dimethyl-4-oxo-cyclohexyl ester

4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone

1-methyl-1,4-cyclohexanediol

4-hydroxy-4-methylcyclohexanone

Refernces