Methyl 3-cyclohexylprop-2-ynoate

Base Information

• Chemical Name: Methyl 3-cyclohexylprop-2-ynoate
• CAS No.: 42134-60-1
• Molecular Formula: C10H14O2
• Molecular Weight: 166.22
• DSSTox Substance ID: DTXSID20702054
• Nikkaji Number: J89.442G
• Wikidata: Q82633855
• Mol file: 42134-60-1.mol

Synonyms:42134-60-1;methyl 3-cyclohexylprop-2-ynoate;methyl 3-cyclohexylpropiolate;methyl3-cyclohexylprop-2-ynoate;SCHEMBL14336987;DTXSID20702054;AKOS013859891;3-Cyclohexylpropynoic acid methyl ester;CS-0371491;EN300-787195

Chemical Property of Methyl 3-cyclohexylprop-2-ynoate

Chemical Property:

• PSA: 26.30000
• LogP: 1.74310
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 213

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C#CC1CCCCC1

Technology Process of Methyl 3-cyclohexylprop-2-ynoate

There total 4 articles about Methyl 3-cyclohexylprop-2-ynoate 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: 96.0%

2-cyclohexylacetylene (931-48-6) + methyl chloroformate (79-22-1) → cyclohexylpropynoic acid methyl ester (42134-60-1)

Guidance literature:

2-cyclohexylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.201105517

Reference yield:

cyclohexylpropiolic acid (4361-27-7) + methyl iodide (74-88-4) → cyclohexylpropynoic acid methyl ester (42134-60-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 12h;

DOI:10.1002/1099-0690(200107)2001:13<2507::aid-ejoc2507>3.0.co;2-p

Reference yield:

2-cyclohexylacetylene (931-48-6) → cyclohexylpropynoic acid methyl ester (42134-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tetrabutylammonium tetrafluoroborate; Mg anode; Ag cathode / dimethylformamide / 3 h / 20 °C / 380.03 Torr / Electrochemical reaction

2: K₂CO₃ / dimethylformamide / 12 h / 50 °C

With tetrabutylammonium tetrafluoroborate; silver; potassium carbonate; magnesium; In N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200107)2001:13<2507::aid-ejoc2507>3.0.co;2-p

upstream raw materials:

cyclohexylpropiolic acid

methyl iodide

2-cyclohexylacetylene

methyl chloroformate

Downstream raw materials:

(E)-2,4-dicyclohexyl-5-[(triisopropylsilanyl)methylene]cyclopenta-1,3-diene-1,3-dicarboxylic acid dimethyl ester

methyl (2Z)-2-(cyclohexyl(dimethyl(phenyl)silyl)methylene)pent-4-enoate

cyclohexyl-propiolic acid amide

Refernces

• 1、 Grams, R. Justin,Garcia, Christopher J.,Szwetkowski, Connor,Santos, Webster L.. "Catalytic, transition-metal-free semireduction of propiolamide derivatives: Scope and mechanistic investigation". supporting information. p. 7013 - 7018. Retrieved 2020/09/12.
• 2、 Fritzemeier, Russell,Gates, Ashley,Guo, Xueying,Lin, Zhenyang,Santos, Webster L.. "Transition Metal-Free Trans Hydroboration of Alkynoic Acid Derivatives: Experimental and Theoretical Studies". . p. 10436 - 10444. Retrieved 2018/07/21.