(2S)-2beta-Allyl-3alpha-methylcyclohexanone

Base Information

• Chemical Name: (2S)-2beta-Allyl-3alpha-methylcyclohexanone
• CAS No.: 61674-94-0
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• DSSTox Substance ID: DTXSID20457517
• Nikkaji Number: J283.249F
• Wikidata: Q82280381
• Mol file: 61674-94-0.mol

Synonyms:61674-94-0;(2S)-2beta-Allyl-3alpha-methylcyclohexanone;(2S,3R)-3-methyl-2-prop-2-enylcyclohexan-1-one;SCHEMBL14503064;DTXSID20457517

Chemical Property of (2S)-2beta-Allyl-3alpha-methylcyclohexanone

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC(=O)C1CC=C
• Isomeric SMILES: C[C@@H]1CCCC(=O)[C@H]1CC=C

Technology Process of (2S)-2beta-Allyl-3alpha-methylcyclohexanone

There total 4 articles about (2S)-2beta-Allyl-3alpha-methylcyclohexanone 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%

2-allyl-cyclohex-2-enone (38019-50-0) + methyllithium (917-54-4) → trans-3-Methyl-2-(2-propenyl)cyclohexanone (61674-94-0,795275-74-0)

Guidance literature:

2-allyl-cyclohex-2-enone; methyllithium; With copper(l) iodide; In diethyl ether; hexane; at -78 ℃; for 1h;

With methyl salicylate; In diethyl ether; hexane; at -78 - 20 ℃;

DOI:10.1002/hlca.200390151

Reference yield:

cyclohexenone (930-68-7) + Allyl acetate (591-87-7) + dimethyl zinc(II) (544-97-8) → (2R,3S)-(-)-2-allyl-3-methylcyclohexan-1-one (351904-17-1,795275-74-0) + cis-2-Allyl-3-methyl-cyclohexanon (56620-95-2,61674-93-9,61674-94-0,795275-74-0)

Guidance literature:

cyclohexenone; (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-[(1R)-1-phenethyl]amine; copper(II) bis(trifluoromethanesulfonate); In toluene; at -30 ℃;

dimethyl zinc(II); In toluene; at -30 ℃;

Allyl acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 0 ℃; Further stages.;

DOI:10.1039/b100283j

Reference yield:

3-Methyl-2-(phenylseleno)cyclohexanone (73824-95-0,73824-98-3) + allyltributylstanane (24850-33-7) → cis-3-Methyl-2-(2-propenyl)cyclohexanone (61674-93-9,795275-74-0) + trans-3-Methyl-2-(2-propenyl)cyclohexanone (61674-94-0,795275-74-0)

Guidance literature:

In benzene; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Irradiation;

DOI:10.1021/jo00291a033

upstream raw materials:

cyclohexenone

Allyl acetate

dimethyl zinc(II)

3-Methyl-2-(phenylseleno)cyclohexanone

Downstream raw materials:

2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoate

2-{[(1RS,2SR,3SR)-2-allyl-1,3-dimethylcyclohexyl]oxy}ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

(7R,10E,12aR,13R,16aS)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione

(7R,10E,12aS,13S,16aR)-7-[(1R)-1-(benzyloxy)ethyl]-2,3,6,7,12a,13,14,15,16,16a-decahydro-13,16a-dimethyl-5H-1,4,8-benzotrioxacyclotetradecine-5,9(12H)-dione