Triethyl(penta-1,4-dien-3-yloxy)silane

Base Information

• Chemical Name: Triethyl(penta-1,4-dien-3-yloxy)silane
• CAS No.: 62418-65-9
• Molecular Formula: C11H22OSi
• Molecular Weight: 198.381
• European Community (EC) Number: 633-098-4
• DSSTox Substance ID: DTXSID30407563
• Nikkaji Number: J2.619.810K
• Wikidata: Q82212863
• Mol file: 62418-65-9.mol

Synonyms:62418-65-9;triethyl(penta-1,4-dien-3-yloxy)silane;3-TRIETHYLSILOXY-1,4-PENTADIENE;3-(TRIETHYLSILYLOXY)-1,4-PENTADIENE;SCHEMBL4390926;DTXSID30407563;3-triethylsilyloxypenta-1 ,4-diene;AKOS006228881

Chemical Property of Triethyl(penta-1,4-dien-3-yloxy)silane

Chemical Property:

• Refractive Index: n20/D 1.439
• Boiling Point: 74-75 °C/14 mmHg
• Flash Point: 58 °C
• PSA: 9.23000
• LogP: 3.74880
• Storage Temp.: 2-8°C
• Solubility.: sol pentane, benzene, THF, ether, CH2Cl2.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 198.143991855
• Heavy Atom Count: 13
• Complexity: 145

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC[Si](CC)(CC)OC(C=C)C=C
• Physical properties: bp 140°C; n20D 1.4390.
• Uses: 3-Triethylsilyloxy-1,4-pentadiene is used as a masked vinyl ketone synthon; a precursor for either the diene or dienophile in the intramolecular Diels–Alder reaction.) It may be used to prepare the useful 3-triethylsilyloxypentadienyl anion via metalation with sec-butyllithium (eq 1).A wide variety of electrophiles may be used and the selectivity is based on kinetics.The method has been used to prepare intermediates for intramolecular Diels–Alder reactions (eqs 4 and 5).

Technology Process of Triethyl(penta-1,4-dien-3-yloxy)silane

There total 1 articles about Triethyl(penta-1,4-dien-3-yloxy)silane 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: 88.0%

divinylcarbinol (922-65-6) + triethylsilyl chloride (994-30-9) → Triethyl<(1,4-pentadien-3-yl)oxy>silan (62418-65-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 15h;

DOI:10.1002/hlca.19810640705

Reference yield: 92.0%

Triethyl<(1,4-pentadien-3-yl)oxy>silan (62418-65-9) → divinylcarbinol (922-65-6)

Guidance literature:

With Selectfluor; In acetonitrile; at 150 ℃; for 0.05h; Microwave irradiation;

DOI:10.1021/jo802494t

Reference yield:

Triethyl<(1,4-pentadien-3-yl)oxy>silan (62418-65-9) → octyl vinyl ketone (42832-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sec-BuLi / tetrahydrofuran; cyclohexane / -78 °C

2: 78 percent / KF / methanol / 3 h / -5 °C

With potassium fluoride; sec.-butyllithium; In tetrahydrofuran; methanol; cyclohexane;

DOI:10.1002/hlca.19810640705

upstream raw materials:

divinylcarbinol

triethylsilyl chloride

Downstream raw materials:

3-benzyl-3-triethylsilyloxy-1,4-pentadiene

(Z)-1,1-diphenyl-4-triethylsilyloxy-3,5-hexadien-1-ol

C₂₄H₃₄OSi₂

(Z)-1-(3-triethylsilyloxy-2,4-pentadienyl)-1-cyclohexanol

Refernces

• 1、 Oppolzer, Wolfgang,Snowden, Roger L.,Simmons, Dana P.. "3-Triethylsilyloxypentadienyllithium, a Versatile 1,3-Diene- or Vinyl ketone-Building Block". . p. 2002 - 2021. Retrieved 2007/10/02.