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:

97% ^*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
• General Description: 1-Methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky-Kitahara diene) is an electron-rich conjugated diene that participates in [4+2]-cycloaddition reactions with ketenes to form dihydropyrans, which subsequently rearrange to yield 4-pyrones. Its electron-donating methoxy and trimethylsiloxy substituents stabilize dipolar intermediates during the cycloaddition, facilitating the efficient synthesis of 4-pyrones in a single-step process. This diene is particularly useful in ketene-based cycloadditions due to its reactivity and ability to promote the formation of heterocyclic products.

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

<4+2>-Cycloaddition Reactions of Ketenes: A Novel Synthesis of 4-Pyrones

10.1055/s-1982-29856

The research investigates the [4+2]-cycloaddition reactions of ketenes with electron-rich conjugated dienes to synthesize 4-pyrones. The study explores the cycloaddition of various ketenes, including dichloro- (2a), chloro- (2b), and diphenylketenes (2c), with dienes such as 1-methoxy-3-trimethylsiloxy-1,3-butadiene (la) and 2,4-bis[trimethylsiloxy]-1,3-pentadiene (1b). The cycloaddition products initially form dihydropyrans, which then undergo a facile rearrangement to yield the desired 4-pyrones. The reaction mechanism is proposed to occur through a dipolar intermediate, with the electron-donating substituents on the conjugated diene stabilizing the positive charge in this intermediate. The resulting 4-pyrones are obtained through a relatively simple one-step preparation, offering an attractive alternative to traditional multi-step syntheses. The study highlights the general applicability of this reaction for ketenes and electron-rich conjugated dienes with specific substituents.