Cinnamyl isovalerate

Base Information

• Chemical Name: Cinnamyl isovalerate
• CAS No.: 140-27-2
• Molecular Formula: C14H18O2
• Molecular Weight: 218.296
• Hs Code.: 2942000000
• European Community (EC) Number: 205-407-9
• NSC Number: 46141
• UNII: 5JHK9Y2XRM
• Nikkaji Number: J503.383G,J105.390F
• Wikidata: Q27262438
• ChEMBL ID: CHEMBL4162391
• Mol file: 140-27-2.mol

Synonyms:cinnamyl isovalerate

Chemical Property of Cinnamyl isovalerate

Chemical Property:

• Vapor Pressure: 0.000269mmHg at 25°C
• Refractive Index: 1.53
• Boiling Point: 323.014 °C at 760 mmHg
• Flash Point: 128.316 °C
• PSA: 26.30000
• Density: 1.007 g/cm³
• LogP: 3.28910
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 218.130679813
• Heavy Atom Count: 16
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

Cinnamyl Isovalerate >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)OCC=CC1=CC=CC=C1
• Isomeric SMILES: CC(C)CC(=O)OC/C=C/C1=CC=CC=C1

Technology Process of Cinnamyl isovalerate

There total 6 articles about Cinnamyl isovalerate 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: 79.0%

3-Phenylpropenol (104-54-1) + isopentanoyl chloride (108-12-3) → cinnamyl 3-methylbutanoate (140-27-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; Reflux;

DOI:10.1002/cbdv.200800310

Reference yield: 75.0%

3-methylbutyric acid (503-74-2) + 3-Phenylpropenol (104-54-1) → cinnamyl 3-methylbutanoate (140-27-2)

Guidance literature:

With dmap; pivaloyl chloride; In dichloromethane; at 100 ℃; Microwave irradiation;

DOI:10.1080/00397911.2011.640970

Reference yield: 63.0%

(S)-cinnamyl 2-bromo-3-methylbutanoate → 2-isopropyl-3-phenylpent-4-enoic acid (1310051-05-8) + cinnamyl 3-methylbutanoate (140-27-2)

Guidance literature:

(S)-cinnamyl 2-bromo-3-methylbutanoate; With tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; indium(III) chloride; indium; chloro-trimethyl-silane; triethylamine; at 10 - 30 ℃; Inert atmosphere; Sonication;

With water; ammonium chloride; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; optical yield given as %de; diastereoselective reaction; Saturated solution;

DOI:10.1016/j.tet.2011.03.079

upstream raw materials:

3-Phenylpropenol

isopentanoyl chloride

L-valine

2S-2-bromo-3-methylbutanoic acid

Refernces

• 1、 Perdomo, Igor Chiarelli,Gianolio, Stefania,Pinto, Andrea,Romano, Diego,Contente, Martina Letizia,Paradisi, Francesca,Molinari, Francesco. "Efficient Enzymatic Preparation of Flavor Esters in Water". . p. 6517 - 6522. Retrieved 2019/06/20.
• 2、 Ishihara, Jun,Watanabe, Yuki,Koyama, Noriko,Nishino, Yukihiro,Takahashi, Keisuke,Hatakeyama, Susumi. "Indium-mediated Reformatsky-Claisen rearrangement". experimental part. p. 3659 - 3667. Retrieved 2011/06/21.