Methyl Cyclohex-2-ene-1-carboxylate

Base Information

• Chemical Name: Methyl Cyclohex-2-ene-1-carboxylate
• CAS No.: 25662-37-7
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Hs Code.: 2916209090
• DSSTox Substance ID: DTXSID40451592
• Nikkaji Number: J88.371I
• Wikidata: Q82271679
• Metabolomics Workbench ID: 94856
• Mol file: 25662-37-7.mol

Synonyms:Methyl Cyclohex-2-ene-1-carboxylate;25662-37-7;2-Cyclohexene-1-carboxylic acid, methyl ester;methyl cyclohex-2-enecarboxylate;starbld0039942;methyl tetrahydrobenzoate;SCHEMBL823220;DTXSID40451592;LKVHTVRTQUBZDN-UHFFFAOYSA-N;Methyl 2-cyclohexene-1-carboxylate;2-Cyclohexene-1-carboxylic acid methyl ester;EN300-6237205

Chemical Property of Methyl Cyclohex-2-ene-1-carboxylate

Chemical Property:

• PSA: 26.30000
• LogP: 1.51570
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 140.083729621
• Heavy Atom Count: 10
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCC=C1

Technology Process of Methyl Cyclohex-2-ene-1-carboxylate

There total 27 articles about Methyl Cyclohex-2-ene-1-carboxylate 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: 86.0%

methanol (67-56-1) + 2-(cyclohex-2-enyl)malononitrile (6904-13-8,150921-95-2,150921-96-3) → methyl cyclohex-2-en-1-carboxylate (25662-37-7)

Guidance literature:

With lithium carbonate; magnesium bis(monoperoxyphthalate) hexahydrate; at 0 ℃; for 3h; optical yield given as %ee;

DOI:10.1055/s-0028-1083540

Reference yield:

6-oxabicyclo[3.2.1]oct-3-en-7-one (4720-83-6) → methyl cyclohex-2-en-1-carboxylate (25662-37-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / sodium methoxide / 10 h / Ambient temperature

2: 77 percent / perchloric acid / ethyl acetate; H₂O / 2 h / Ambient temperature

3: 70 percent / sodium methoxide / methanol / 7.5 h / Ambient temperature

4: 40 percent / sodium methoxide / benzene / 3 h / Heating

5: pyridine / 9 h / Ambient temperature

6: trimethylammonium acetate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3.5 h / Heating

With pyridine; perchloric acid; trimethylammonium acetate; sodium methylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; water; ethyl acetate; benzene;

DOI:10.1021/ja00534a029

Reference yield:

methyl 5-hydroxy-3-cyclohexenecarboxylate (79433-96-8) → methyl cyclohex-2-en-1-carboxylate (25662-37-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / sodium methoxide / benzene / 3 h / Heating

2: pyridine / 9 h / Ambient temperature

3: trimethylammonium acetate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 3.5 h / Heating

With pyridine; trimethylammonium acetate; sodium methylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; benzene;

DOI:10.1021/ja00534a029

upstream raw materials:

methanol

cyclohex-2-ene-1-carboxylic acid

(1S*,2S*)-2-(methoxycarbonyl)cyclohexane-1-carboxylic acid

cyclohexane-1,2-dicarboxylic acid monomethyl ester

Downstream raw materials:

methyl cyclohex-1-ene-1-carboxylate

1-(3-Iodo-2-iodomethyl-propyl)-cyclohex-2-enecarboxylic acid methyl ester

methyl 1-(Z-3'-iodo-2'-hepten-1'-yl)-2-cyclohexene-1-carboxylate

bicyclohexyl-2,2'-diene

Refernces

• 1、 Leiris, Simon,Lucas, Marc,Dupuy D'Angeac, Arnaud,Morre, Alain. "Synthesis and biological evaluation of cyclic nitrogen mustards based on carnitine framework". experimental part. p. 4140 - 4148. Retrieved 2010/10/02.
• 2、 Hutchison, Tracy L.,Saeed, Ashraf,Wolkowicz, Paul E.,McMillin, Jeanie B.,Brouillette, Wayne J.. "Stereoselective synthesis of a conformationally defined cyclohexyl carnitine analogue that binds CPT-1 with high affinity". . p. 1505 - 1511. Retrieved 2007/10/03.