1-Methoxy-3-trimethylsiloxy-1,3-butadiene

Base Information

• Chemical Name: 1-Methoxy-3-trimethylsiloxy-1,3-butadiene
• CAS No.: 54125-02-9
• Molecular Formula: C8H16 O2 Si
• Molecular Weight: 172.299
• Hs Code.: 2931900090
• European Community (EC) Number: 261-753-0,629-035-5
• UNII: 1ZOR63U51O
• DSSTox Substance ID: DTXSID5069330,DTXSID10202472
• Nikkaji Number: J364.538J,J341G
• Wikipedia: Danishefsky%27s_diene,Danishefsky's_diene
• Wikidata: Q904983
• Mol file: 54125-02-9.mol

Synonyms:1-methoxy-3-trimethylsilyloxy-1,3-butadiene

Chemical Property of 1-Methoxy-3-trimethylsiloxy-1,3-butadiene

Chemical Property:

• Refractive Index: n20/D 1.454(lit.)
• Boiling Point: 181.7°Cat760mmHg
• Flash Point: 59 ºC
• PSA: 18.46000
• Density: 0.885
• LogP: 2.51170
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Miscible with most organic solvents. Immiscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 172.091956283
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

99.0% ^*data from raw suppliers

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene 95% ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC=CC(=C)O[Si](C)(C)C
• Isomeric SMILES: CO/C=C/C(=C)O[Si](C)(C)C
• Uses: 1-Methoxy-3-trimethylsiloxy-1,3-butadiene is employed as a reagent in Mannich-Michael reaction for the synthesis of piperidinones and enaminones. As Diels-Alder diene, it is used in the synthesis of pyridones and pyranones, sulfone analogues of griseofulvin (sulfogriseofulvins) and 4H-1-aminopyrroles and 4, 5H-pyrazoles.

Technology Process of 1-Methoxy-3-trimethylsiloxy-1,3-butadiene

There total 4 articles about 1-Methoxy-3-trimethylsiloxy-1,3-butadiene 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: 87.0%

chloro-trimethyl-silane (75-77-4) + trans-4-methoxy-3-buten-2-one (51731-17-0) → danishefsky's diene (54125-02-9)

Guidance literature:

With triethylamine; zinc(II) chloride; In benzene; at 40 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol901902v

Reference yield:

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + trans-4-methoxy-3-buten-2-one (51731-17-0) → danishefsky's diene (54125-02-9)

Guidance literature:

In diethyl ether; at 0 ℃; for 5h;

DOI:10.1021/ja028186k

Reference yield:

chloro-trimethyl-silane (75-77-4) + 4-methoxy-3-buten-2-one → danishefsky's diene (54125-02-9)

Guidance literature:

With triethylamine; zinc(II) chloride;

DOI:10.1021/ja00832a031

upstream raw materials:

chloro-trimethyl-silane

trans-4-methoxy-3-buten-2-one

trimethylsilyl trifluoromethanesulfonate

4-methoxy-3-buten-2-one

Downstream raw materials:

4-methyl-4-formylcyclohex-2-enone

trans-1-Methoxy-4-phenylsebnobut-1-en-3-on

4-Acetylcyclohex-3-en-2-on

methyl 1-methyl-4-oxo-2-cyclohexene-1-carboxylate

Refernces

• 1、 Guo, Hongchao,Wang, Zheng,Ding, Kuiling. "PEG-polymer-supported liquid-phase combinatorial synthesis of structurally diverse 2,3-dihydro-4-pyridones". . p. 1061 - 1068. Retrieved 2005.
• 2、 Jin, Da-Ping,Gao, Zhu-Peng,Liu, Lin,Cao, Shi-Qi,Xu, Xue-Tao,Hou, Xue-Wei,Zheng, Tian-Lu,Jiang, Li-Ming,Zhu, Dao-Yong,Wang, Shao-Hua. "Total Synthesis of (±)-Furanether A". supporting information. p. 8843 - 8846. Retrieved 2021/11/20.