Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (5R)-

Base Information

• Chemical Name: Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (5R)-
• CAS No.: 116499-64-0
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Mol file: 116499-64-0.mol

Synonyms:

Chemical Property of Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (5R)-

There total 97 articles about Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (5R)- 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: 95.0%

Carvone (99-49-0,22327-39-5) → 2-methyl-5-(prop-1-en-2-yl)cyclohexanone (3792-53-8,4584-09-2,5524-05-0,5948-04-9,6909-25-7,7764-50-3,53796-79-5,69460-46-4,116499-64-0,619-02-3,619-01-2)

Guidance literature:

With tri-n-butyl-tin hydride; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)86751-9

Reference yield: 85.0%

9-isopropenyl-6-methyl-1,4-dioxa-spiro[4.5]decane (22344-27-0) → 2-methyl-5-(prop-1-en-2-yl)cyclohexanone (3792-53-8,4584-09-2,5524-05-0,5948-04-9,6909-25-7,7764-50-3,53796-79-5,69460-46-4,116499-64-0,619-02-3,619-01-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -20 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.10.037

Reference yield: 79.0%

limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3) → 2-methyl-5-(prop-1-en-2-yl)cyclohexanone (3792-53-8,4584-09-2,5524-05-0,5948-04-9,6909-25-7,7764-50-3,53796-79-5,69460-46-4,116499-64-0,619-02-3,619-01-2)

Guidance literature:

limonene.; With Acetoxyboran; In tetrahydrofuran; at 20 ℃; for 16h;

With pyridinium chlorochromate; In dichloromethane; for 1h; Heating;

upstream raw materials:

(S)-p-mentha-6,8-dien-2-one

(1S,2S,5S)-5-isopropenyl-2-methylcyclohexan-1-ol

(S)-p-mentha-6,8-dien-2-one-(Z)-oxime

Limonene oxide

Downstream raw materials:

p-Menth-2,9-diol

(1S,4R,8R)-1,8,9-tribromo-p-menthan-2-one

p-menth-3-en-2-one

(2S,5R,E)-dihydrocarvone oxime

Refernces

• 1、 Cortés, DIego A.,Elrod, Matthew J.. "Kinetics of the Aqueous Phase Reactions of Atmospherically Relevant Monoterpene Epoxides". . p. 9297 - 9305. Retrieved 2017.
• 2、 Moreno-Marrodan, Carmen,Barbaro, Pierluigi,Catalano, Massimo,Taurino, Antonietta. "Green production of polymer-supported PdNPs: Application to the environmentally benign catalyzed synthesis of cis-3-hexen-1-ol under flow conditions". . p. 12666 - 12669. Retrieved 2012.
• 3、 Fleming,I.,Paterson,I.. "-". . p. 736 - 738. Retrieved 1979.
• 4、 Guo, Jiyang,Zhang, Rui,Ouyang, Jingping,Zhang, Feiting,Qin, Fengyu,Liu, Guigao,Zhang, Wenhe,Li, Hengyu,Ji, Xiaohong,Jia, Xian,Qin, Bin,You, Song. "Stereodivergent Synthesis of Carveol and Dihydrocarveol through Ketoreductases/Ene-Reductases Catalyzed Asymmetric Reduction". . p. 5496 - 5504. Retrieved 2018.
• 5、 Reger et al.. "-". . p. 115. Retrieved 1979.
• 6、 Bettadaiah,Gurudutt,Srinivas. "Direct conversion of tert-β-bromo alcohols to ketones with zinc sulfide and DMSO". . p. 2460 - 2462. Retrieved 2003.
• 7、 Collman. "-". . p. 342,343, 344. Retrieved 1975.
• 8、 Silva, Vanessa Dutra,Stambuk, Boris Ugarte,Nascimento, Maria Da Graa. "Asymmetric reduction of (4R)-(-)-carvone catalyzed by Baker's yeast in aqueous mono- and biphasic systems". . p. 98 - 104. Retrieved 2012.
• 9、 Magnus,Waring,Scott. "Conjugate reduction of α,β-unsaturated ketones using an Mn(III) catalyst, phenylsilane and isopropyl alcohol". . p. 9731 - 9733. Retrieved 2000.
• 10、 Rüthi, Fabian,Schr?der, Fridtjof. "Total Synthesis of (?)-Rotundone and (?)-epi-Rotundone from Monoterpene Precursors". . . Retrieved 2020.