Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane

Base Information

• Chemical Name: Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane
• CAS No.: 182801-94-1
• Molecular Formula: C21H26OSi
• Molecular Weight: 322.522
• DSSTox Substance ID: DTXSID70463163
• Nikkaji Number: J1.738.808H
• Mol file: 182801-94-1.mol

Synonyms:182801-94-1;tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane;Benzene, 1,1'-[(3-cyclopenten-1-yloxy)(1,1-dimethylethyl)silylene]bis-;tert-butyl-cyclopent-3-en-1-yloxy-diphenylsilane;MFCD22570650;C21H26OSi;SCHEMBL1139424;DTXSID70463163;GCODZQWZNXYLIA-UHFFFAOYSA-N;Silane, (3-cyclopenten-1-yloxy)(1,1-dimethylethyl)diphenyl-;AKOS037647163;AS-72675;SY125159;CS-0037373;FT-0720940;tert-Butyl(3-cyclopenten-1-yloxy)diphenylsilane;W13348;3-cyclopenten-1-yl (t-butyldiphenylsilyl) ether

Chemical Property of Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 322.175291983
• Heavy Atom Count: 23
• Complexity: 371

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OC3CC=CC3

Technology Process of Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane

There total 5 articles about Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane 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: 100.0%

cyclopent-3-enol (14320-38-8) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl(diphenyl)silyl 3-cyclopenten-1-yl ether (182801-94-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2003.09.024

Reference yield: 98.0%

4-(tert-butyldiphenylsilyloxy)hepta-1,6-diene (175164-50-8) → tert-butyl(diphenyl)silyl 3-cyclopenten-1-yl ether (182801-94-1)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 2h; Reflux;

DOI:10.1039/b809178a

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl(diphenyl)silyl 3-cyclopenten-1-yl ether (182801-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: 4 h / 23 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / Reflux

With sodium hydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; mineral oil;

upstream raw materials:

cyclopent-3-enol

tert-butylchlorodiphenylsilane

4-(tert-butyldiphenylsilyloxy)hepta-1,6-diene

1, 6-heptadien-4-ol

Downstream raw materials:

trans-3-(tert-butyldiphenylsilyloxy)-6-oxa-bicyclo[3.1.0]hexane

cis-3-(tert-butyldiphenylsilyloxy)-6-oxa-bicyclo[3.1.0]hexane

cis-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(4-methylphenyl)sulfonyl]-6-azabicyclo[3.1.0]hexane

(1S,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-cyclopent-2-enol