2-Butenoic acid, 4-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)cyclohexyl)-2-methyl-, methyl ester, (1alpha(E),2beta)-

Base Information

• Chemical Name: 2-Butenoic acid, 4-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)cyclohexyl)-2-methyl-, methyl ester, (1alpha(E),2beta)-
• CAS No.: 101859-22-7
• Molecular Formula: C18H34 O3 Si
• Molecular Weight: 326.5463
• Mol file: 101859-22-7.mol

Synonyms:101859-22-7;2-Butenoic acid, 4-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)cyclohexyl)-2-methyl-, methyl ester, (1alpha(E),2beta)-

Chemical Property of 2-Butenoic acid, 4-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)cyclohexyl)-2-methyl-, methyl ester, (1alpha(E),2beta)-

Chemical Property:

• Vapor Pressure: 2.34E-05mmHg at 25°C
• Boiling Point: 359.7°C at 760 mmHg
• Flash Point: 142.4°C
• Density: 0.94g/cm³
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 326.22772148
• Heavy Atom Count: 22
• Complexity: 407

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1CCCCC1O[Si](C)(C)C(C)(C)C)C(=O)OC
• Isomeric SMILES: C/C(=C\C[C@H]1CCCC[C@@H]1O[Si](C)(C)C(C)(C)C)/C(=O)OC

Technology Process of 2-Butenoic acid, 4-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)cyclohexyl)-2-methyl-, methyl ester, (1alpha(E),2beta)-

There total 4 articles about 2-Butenoic acid, 4-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)cyclohexyl)-2-methyl-, methyl ester, (1alpha(E),2beta)- 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: 90.0%

(2-t-butyldimethylsiloxy)cyclohexylacetaldehyde (101859-27-2) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → (E)-4-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-methyl-but-2-enoic acid methyl ester (101859-22-7)

Guidance literature:

In chloroform; Heating;

DOI:10.1021/jo00362a014

Reference yield:

(1R*,2S*)-2-hydroxycyclohexane acetonitrile (74708-24-0,74708-25-1,90242-33-4,101976-91-4,74629-88-2) → (E)-4-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-methyl-but-2-enoic acid methyl ester (101859-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / TEA, DMAP / tetrahydrofuran; dimethylformamide

2: 86 percent / dibal / toluene / -78 - 0 °C

3: 90 percent / CHCl₃ / Heating

With dmap; TEA; diisobutylaluminium hydride; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00362a014

Reference yield:

cyclohexane-1,2-epoxide (286-20-4) → (E)-4-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-2-methyl-but-2-enoic acid methyl ester (101859-22-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / tetrahydrofuran / 0 °C

2: 88 percent / TEA, DMAP / tetrahydrofuran; dimethylformamide

3: 86 percent / dibal / toluene / -78 - 0 °C

4: 90 percent / CHCl₃ / Heating

With dmap; TEA; diisobutylaluminium hydride; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00362a014

upstream raw materials:

(2-t-butyldimethylsiloxy)cyclohexylacetaldehyde

methyl 2-(triphenylphosphoranylidene)propionate

(1R*,2S*)-2-hydroxycyclohexane acetonitrile

cyclohexane-1,2-epoxide

Downstream raw materials:

(1R*,2S*,(2E))-2-((tert-butyldimethylsilyl)oxy)cyclohexane-3-methyl-2-buten-4-ol

4-<(1RS,2SR)-2-hydroxycyclohexyl>-2-methylbut-2(E)-enyl 2,4-dichlorobenzoate

2,4-Dichloro-benzoic acid (E)-4-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-2-methyl-but-2-enyl ester

tert-Butyl-{(1R,2S)-2-[(E)-4-(2,6-dichloro-benzyloxy)-3-methyl-but-2-enyl]-cyclohexyloxy}-dimethyl-silane

Refernces