(3S,4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate

Base Information

• Chemical Name: (3S,4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate
• CAS No.: 136314-66-4
• Molecular Formula: C15H22O2Si
• Molecular Weight: 262.424
• European Community (EC) Number: 663-771-8
• Nikkaji Number: J428.636G,J811.841H
• Mol file: 136314-66-4.mol

Synonyms:(3S,4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate;136314-66-4;methyl (E,3S)-3-[dimethyl(phenyl)silyl]hex-4-enoate;Methyl (S)-3-(dimethyl(phenyl)silyl)hex-4-enoate;Methyl(S,E)-3-(dimethyl(phenyl)silyl)hex-4-enoate;Methyl (S,E)-3-(dimethyl(phenyl)silyl)hex-4-enoate;1004309-92-5

Chemical Property of (3S,4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate

Chemical Property:

• Refractive Index: n20/D 1.511
• Boiling Point: 327.7±35.0 °C(Predicted)
• Flash Point: >110°C
• PSA: 26.30000
• Density: 0.984 g/mL at 25 °C
• LogP: 3.11140
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 262.138906475
• Heavy Atom Count: 18
• Complexity: 291

Purity/Quality:

(3S,4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(CC(=O)OC)[Si](C)(C)C1=CC=CC=C1
• Isomeric SMILES: C/C=C/[C@H](CC(=O)OC)[Si](C)(C)C1=CC=CC=C1

Technology Process of (3S,4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate

There total 2 articles about (3S,4E)-Methyl 3-(dimethylphenylsilyl)-4-hexenoate 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: 86.0%

Trimethyl orthoacetate (1445-45-0) + (E)-(3S)-1-(dimethylphenylsilyl)-1-buten-3-ol (133398-24-0) → methyl (3S,4E)-3-(dimethylphenylsilyl)-4-hexenoate (136314-66-4)

Guidance literature:

With propionic acid; In toluene; for 48h; Reflux;

DOI:10.15227/orgsyn.075.0078

Reference yield:

(E)-4-(Dimethyl-phenyl-silanyl)-3-methyl-but-3-en-2-ol (173831-06-6) → methyl (3S,4E)-3-(dimethylphenylsilyl)-4-hexenoate (136314-66-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Pseudomonas lipase AK / pentane / 20 °C

2: propionic acid / toluene / 16 h / Heating

With Pseudomonas lipase AK; propionic acid; In toluene; pentane;

DOI:10.1016/S0040-4020(00)00870-X

Reference yield: 92.0%

methyl (3S,4E)-3-(dimethylphenylsilyl)-4-hexenoate (136314-66-4) + phenylacetaldehyde dimethyl acetal (101-48-4) → (E)-(5R, 6S)-methyl 6-methoxy-7-phenyl-5-methylhept-3-enoate (194149-67-2) + (E)-(5S,6R)-6-Methoxy-5-methyl-7-phenyl-hept-3-enoic acid methyl ester

Guidance literature:

With boron trifluoride diethyl etherate; at -78 - -50 ℃; for 12h;

DOI:10.1021/ja0206700

upstream raw materials:

Trimethyl orthoacetate

(E)-(3S)-1-(dimethylphenylsilyl)-1-buten-3-ol

(E)-4-(Dimethyl-phenyl-silanyl)-3-methyl-but-3-en-2-ol

Downstream raw materials:

(E)-(5S,6R)-7-Benzyloxy-6-methoxy-5-methyl-hept-3-enoic acid methyl ester

(E)-(2R,3R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-hex-4-enoic acid methyl ester

(2S,3R)-(E)-Methyl 2-benzyl-3-(dimethylphenylsilyl)hex-4-enoate

methyl (2R,3R)-α-azido-β-(dimethylphenylsilyl)-(E)-hex-4-enoate