Methyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate

Base Information

• Chemical Name: Methyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate
• CAS No.: 28043-10-9
• Deprecated CAS: 88269-68-5
• Molecular Formula: C11H18 O2
• Molecular Weight: 182.263
• European Community (EC) Number: 248-792-9
• DSSTox Substance ID: DTXSID4051956
• Nikkaji Number: J250.635A
• Mol file: 28043-10-9.mol

Synonyms:Methyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate;28043-10-9;EINECS 248-792-9;2,6,6-Trimethyl-2-cyclohexene-1-carboxylic acid, methyl ester;2-Cyclohexene-1-carboxylic acid, 2,6,6-trimethyl-, methyl ester;EC 248-792-9;2,6,6-Trimethyl-2-cyclohexene-1-carboxylic acid methyl ester;SCHEMBL1774631;DTXSID4051956;FT-0610510;methyl 2,6,6 - trimethylcyclohex - 2 - ene - 1 - carboxylate

Chemical Property of Methyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.151mmHg at 25°C
• Refractive Index: 1.451
• Boiling Point: 215°Cat760mmHg
• Flash Point: 74.6°C
• PSA: 26.30000
• Density: 0.94g/cm³
• LogP: 2.54190
• Water Solubility.: 229mg/L at 20℃
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 182.130679813
• Heavy Atom Count: 13
• Complexity: 239

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(C1C(=O)OC)(C)C

Technology Process of Methyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate

There total 21 articles about Methyl 2,6,6-trimethylcyclohex-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: 91.0%

(+/-)-α-cyclogeranic acid (564-24-9) + dimethyl sulfate (77-78-1) → methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate (28043-10-9)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 5h;

DOI:10.1016/j.bmcl.2005.11.023

Reference yield: 70.0%

methyl (Z)-7-methyl-3-((trimethylsilyl)methyl)octa-2,6-dienoate (81752-85-4) → methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate (28043-10-9)

Guidance literature:

With tin(IV) chloride; In dichloromethane; water; acetic acid; for 2h; Ambient temperature;

Reference yield: 68.0%

(+/-)-α-cyclogeranic acid (564-24-9) + methyl iodide (74-88-4) → methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate (28043-10-9)

Guidance literature:

With potassium carbonate; In acetone; for 24h; Ambient temperature;

DOI:10.1080/00304949809355262

upstream raw materials:

methyl geranate

methyl 3-methylene-7-methyl-6-octenoate

methyl (+/-)-2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate

methyl (Z)-7-methyl-3-((trimethylsilyl)methyl)octa-2,6-dienoate

Downstream raw materials:

2,6,6-trimethyl-2-cyclohexenyl methyl ketone

(Z)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one

α-damascone

1-(2',6',6'-trimethyl-2'-cyclohexenyl)-3-buten-1-one

Refernces

• 1、 Kadas, Istvan,Arvai, Geza,Horyath, Gabriella. "Improved synthesis of 7,7-dimethyl-1,4-dioxo-2,3,4,5,6,7-hexahydroinden-2-yl-acetic and propionic acid from citral". . p. 79 - 85. Retrieved 1998.
• 2、 Nicolaou,Hale, Christopher R. H.,Nilewski, Christian,Ioannidou, Heraklidia A.,Elmarrouni, Abdelatif,Nilewski, Lizanne G.,Beabout, Kathryn,Wang, Tim T.,Shamoo, Yousif. "Total synthesis of viridicatumtoxin B and analogues thereof: Strategy evolution, structural revision, and biological evaluation". supporting information. p. 12137 - 12160. Retrieved 2014/11/08.
• 3、 Xiong, Yi,Wang, Kuiwu,Pan, Yuanjiang,Sun, Hongxiang,Tu, Jue. "Isolation, synthesis, and anti-tumor activities of a novel class of podocarpic diterpenes". . p. 786 - 789. Retrieved 2007/10/03.