Methyl 4-prop-2-ynylcyclohexanecarboxylate

Base Information

• Chemical Name: Methyl 4-prop-2-ynylcyclohexanecarboxylate
• CAS No.: 250682-81-6
• Molecular Formula: C11H16O2
• Molecular Weight: 180.247
• DSSTox Substance ID: DTXSID00444304
• Mol file: 250682-81-6.mol

Synonyms:250682-81-6;Methyl 4-prop-2-ynylcyclohexanecarboxylate;trans-4-(2-Propynyl)cyclohexanecarboxylic Acid Methyl Ester;Methyl 4-prop-2-ynylcyclohexane-1-carboxylate;Methyl trans-4-(prop-2-yn-1-yl)cyclohexane-1-carboxylate;starbld0006659;SCHEMBL243310;SCHEMBL3425669;SCHEMBL13461145;DTXSID00444304;VFOQETNBTUILTQ-UHFFFAOYSA-N;CS-0492425;FT-0674119;J-015800;4-prop-2-ynyl-cyclohexanecarboxylic acid methyl ester;trans-Methyl 4-(prop-2-yn-1-yl)cyclohexanecarboxylate

Chemical Property of Methyl 4-prop-2-ynylcyclohexanecarboxylate

Chemical Property:

• Boiling Point: 233.4±13.0 °C(Predicted)
• PSA: 26.30000
• Density: 0.990±0.06 g/cm3(Predicted)
• LogP: 1.98910
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Methanol
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 180.115029749
• Heavy Atom Count: 13
• Complexity: 216

Purity/Quality:

98% ^*data from raw suppliers

trans-4-(2-Propynyl)cyclohexanecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(CC1)CC#C

Technology Process of Methyl 4-prop-2-ynylcyclohexanecarboxylate

There total 6 articles about Methyl 4-prop-2-ynylcyclohexanecarboxylate 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: 80.0%

4-prop-2-ynylcyclohexanecarboxylic acid (250682-80-5) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 4-prop-2-ynylcyclohexanecarboxylate (250682-81-6)

Guidance literature:

In methanol; hexane; dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1021/jm0003642

Reference yield:

(4-prop-2-ynylcyclohexyl)methanol (250682-79-2) → methyl 4-prop-2-ynylcyclohexanecarboxylate (250682-81-6)

Guidance literature:

1: Jones oxidation;

DOI:10.1038/sj.bjp.0703893

Reference yield:

trans-1,4-Cyclohexanedimethanol (3236-48-4) → methyl 4-prop-2-ynylcyclohexanecarboxylate (250682-81-6)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide

2: pyridine / CHCl₃

3: tetrabutylammonium fluoride

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; In chloroform; N,N-dimethyl-formamide; 5: Jones oxidation;

DOI:10.1038/sj.bjp.0703893

upstream raw materials:

4-prop-2-ynylcyclohexanecarboxylic acid

diazomethyl-trimethyl-silane

trans-1,4-Cyclohexanedimethanol

(4-prop-2-ynylcyclohexyl)methanol

Downstream raw materials:

(S)-trans-4-[3-(5-(1-Methyl-2-pyrrolidinyl)-2-pyridinyl)prop-2-ynyl]cyclohexanecarboxylic Acid Methyl Ester

Apadenoson

Refernces

• 1、 Rieger,Brown,Sullivan,Linden,Macdonald. "Design, synthesis, and evaluation of novel A2A adenosine receptor agonists". . p. 531 - 539. Retrieved 2007/10/03.