4-((Tert-butyldimethylsilyl)oxy)cyclopent-2-enone

Base Information

• Chemical Name: 4-((Tert-butyldimethylsilyl)oxy)cyclopent-2-enone
• CAS No.: 56745-67-6
• Molecular Formula: C₁₁H₂₀O₂Si
• Molecular Weight: 212.364
• DSSTox Substance ID: DTXSID90399692
• Nikkaji Number: J340.932E
• Mol file: 56745-67-6.mol

Synonyms:4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone;56745-67-6;starbld0018236;SCHEMBL968867;DTXSID90399692;DAPZSGCXUJECAI-UHFFFAOYSA-N;4-t-butyldimethylsilyloxy-2-cyclopentenone;4-tert-butyldimethylsiloxy-2-cyclopentenone;4-t-butyldimethylsiloxycyclopent-2-en-1-one;FT-0600200;4-(t-butyldimethyl-silyloxy)-2-cyclopentenone;4(RS)-t-butyldimethylsilyloxy-2-cyclopentenone;(+/-)-4-tert-butyldimethylsiloxycyclopent-2-en-1-one;4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-one;4-{[tert-Butyl(dimethyl)silyl]oxy}cyclopent-2-en-1-one;4-(TERT-BUTYLDIMETHYLSILYLOXY)-2-CYCLOPENTEN-1-ONE;(RS)-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

Chemical Property of 4-((Tert-butyldimethylsilyl)oxy)cyclopent-2-enone

Chemical Property:

• Boiling Point: 246.128 °C at 760 mmHg
• Flash Point: 85.393 °C
• Density: 0.944 g/cm³
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 212.123256411
• Heavy Atom Count: 14
• Complexity: 261

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](C)(C)OC1CC(=O)C=C1

Technology Process of 4-((Tert-butyldimethylsilyl)oxy)cyclopent-2-enone

There total 8 articles about 4-((Tert-butyldimethylsilyl)oxy)cyclopent-2-enone 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: 79.0%

4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone (61305-35-9,61305-36-0,61740-33-8,56745-67-6) + phenylboronic acid (98-80-6) → (4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one (56745-67-6,61305-35-9,61740-33-8,61305-36-0) + C17H26O2Si

Guidance literature:

4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone; With chlorobis(ethylene)rhodium(I) dimer; C₃₇H₃₃O₃P; cesium fluoride; In 1,4-dioxane; water; at 20 ℃; for 0.25h; Schlenk technique; Inert atmosphere;

phenylboronic acid; In 1,4-dioxane; water; at 20 ℃; for 2h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/adsc.201400459

Reference yield: 44.0%

(+/-)-4-oxocyclopenten-2-enyl 2-phenylacetate (1391630-27-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-4-oxocyclopenten-2-enyl 2-phenylacetate (1391630-29-7) + (4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one (56745-67-6,61305-35-9,61740-33-8,61305-36-0)

Guidance literature:

(+/-)-4-oxocyclopenten-2-enyl 2-phenylacetate; In di-isopropyl ether; for 72h; pH=7.5; aq. phosphate buffer; Enzymatic reaction;

tert-butyldimethylsilyl chloride; With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; optical yield given as %ee; enantioselective reaction; Cooling with ice;

DOI:10.1016/j.tetasy.2012.05.018

Reference yield: 37.0%

4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone (61305-35-9,61305-36-0,61740-33-8,56745-67-6) + phenylboronic acid (98-80-6) → (4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one (56745-67-6,61305-35-9,61740-33-8,61305-36-0) + C17H24O2Si + C17H26O2Si

Guidance literature:

4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone; With chlorobis(ethylene)rhodium(I) dimer; C₃₇H₃₃O₃P; cesium fluoride; In 1,4-dioxane; water; at 20 ℃; for 0.25h; Schlenk technique; Inert atmosphere;

phenylboronic acid; In 1,4-dioxane; water; at 20 ℃; for 2h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/adsc.201400459

upstream raw materials:

(+/-)-4-oxocyclopenten-2-enyl 2-phenylacetate

tert-butyldimethylsilyl chloride

4-Hydroxycyclopent-2-enone

4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone

Downstream raw materials:

Methyl (Z)-7-<(3R)-3-<(tert-Butyldimethylsilyl)oxy>-5-oxo-1-cyclopentenyl>-5-heptenoate

7-[(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-2-phenylsulfanyl-cyclopent-(Z)-ylidene]-hept-5-ynoic acid methyl ester