(S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one

Base Information

• Chemical Name: (S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one
• CAS No.: 145627-30-1
• Molecular Formula: C₂₁H₃₀O₂S
• Molecular Weight: 346.534
• Mol file: 145627-30-1.mol

Synonyms:(S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one

Chemical Property of (S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one

There total 2 articles about (S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one 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: 68.0%

3,3,7-trimethyl-oct-6-enal (17920-90-0) + (+)-(R)-1-(p-tolylsulfinyl)-2-propanone (66536-78-5) → (S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one (145627-30-1)

Guidance literature:

With 4 A molecular sieve; piperdinium acetate; In benzene; for 48h; Ambient temperature;

DOI:10.1248/cpb.41.666

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one (145627-30-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, hexane, 0 deg C, 2 h, 2.) THF, hexane, 0 deg C, 30 min

2: 68 percent / piperidinium acetate, molecular sieves 4A / benzene / 48 h / Ambient temperature

With 4 A molecular sieve; piperdinium acetate; lithium diisopropyl amide; In benzene;

DOI:10.1248/cpb.41.666

Reference yield:

(S)-(+)-3-p-toluenesulfinyl-6,6,10-trimethyl-3,9-undecadien-2-one (145627-30-1) → (1R,2R,αR,Rs)-(+)-1-(5,5-dimethyl-2-isopropylencyclohexyl)-1-p-toluenesulfinyl-2-propanone (145627-33-4) + (1R,2R,αS,Rs)-(-)-1-(5,5-dimethyl-2-isopropenylcyclohexyl)-1-p-toluenesulfinyl-2-propanone (145679-83-0) + (4aR,8aR,SS)-4a,5,6,7,8,8a-hexahydro-1,1,3,6,6-pentamethyl-4-(p-toluenesulfinyl)-1H-2-benzopyran (145627-37-8) + (4aS,8aS,SS)-4a,5,6,7,8,8a-hexahydro-1,1,3,6,6-pentamethyl-4-(p-toluenesulfinyl)-1H-2-benzopyran (145627-31-2)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 ℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)60862-6

upstream raw materials:

3,3,7-trimethyl-oct-6-enal

(+)-(R)-1-(p-tolylsulfinyl)-2-propanone

(R)-methyl p-tolyl sulfoxide

Downstream raw materials:

(1R,2R,αR,Rs)-(+)-1-(5,5-dimethyl-2-isopropylencyclohexyl)-1-p-toluenesulfinyl-2-propanone

(1R,2R,αS,Rs)-(-)-1-(5,5-dimethyl-2-isopropenylcyclohexyl)-1-p-toluenesulfinyl-2-propanone

(4aS,8aR,Ss)-(-)-4a,5,6,7,8,8a-hexahydro-1,1,3,6,6-pentamethyl-4-p-toluenesulfinyl-1H-2-benzopyran

(4aR,8aR,S_S)-4a,5,6,7,8,8a-hexahydro-1,1,3,6,6-pentamethyl-4-(p-toluenesulfinyl)-1H-2-benzopyran