1-Phenyl-3-trimethylsilyloxy-1-propene

Base Information

• Chemical Name: 1-Phenyl-3-trimethylsilyloxy-1-propene
• CAS No.: 109283-53-6
• Molecular Formula: C12H18OSi
• Molecular Weight: 206.36
• DSSTox Substance ID: DTXSID401347982
• Nikkaji Number: J1.091.980K,J882.562I
• Mol file: 109283-53-6.mol

Synonyms:Cinnamyl alcohol, TMS derivative;1-Phenyl-3-trimethylsilyloxy-1-propene;109283-53-6;Cinnamyl(trimethylsilyl) ether;3-Phenylallyloxytrimethylsilane;SCHEMBL8569691;HUAIMAUDFCUWLH-JXMROGBWSA-N;DTXSID401347982;(2E)-3-Phenyl-2-propenyl trimethylsilyl ether #;Trimethyl{[(2E)-3-phenyl-2-propen-1-yl]oxy}silane

Chemical Property of 1-Phenyl-3-trimethylsilyloxy-1-propene

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 206.112691728
• Heavy Atom Count: 14
• Complexity: 175

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OCC=CC1=CC=CC=C1
• Isomeric SMILES: C[Si](C)(C)OC/C=C/C1=CC=CC=C1

Technology Process of 1-Phenyl-3-trimethylsilyloxy-1-propene

There total 18 articles about 1-Phenyl-3-trimethylsilyloxy-1-propene 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: 99.0%

3-Phenylpropenol (104-54-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → trimethylsilyl cinnamyl ether (109283-53-6,141427-94-3,18042-41-6)

Guidance literature:

iodine; In dichloromethane; at 20 ℃; for 0.0333333h;

DOI:10.1021/jo005519s

Reference yield: 99.0%

trimethylsilylazide (4648-54-8) + 3-Phenylpropenol (104-54-1) → trimethylsilyl cinnamyl ether (109283-53-6,141427-94-3,18042-41-6)

Guidance literature:

In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1055/s-1986-31869

Reference yield: 98.0%

trimethylsilylazide (4648-54-8) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (E)-cinnamyloxytrimethylsilane (109283-53-6)

Guidance literature:

tetrabutylammomium bromide; at 30 ℃; for 0.00333333h;

DOI:10.1021/jo015814s

upstream raw materials:

chloro-trimethyl-silane

3-Phenylpropenol

trimethylsilylazide

1,1,1,2,2,2-hexamethyldisilane

Downstream raw materials:

silicic acid tetra-trans-cinnamyl ester

trans-cinnamyl iodide

3-phenyl-1-heptene

(E)-1-heptenylbenzene

Refernces

• 1、 Shirini, Farhad,Zolfigol, Mohammad Ali,Mohammadi, Kamal. "A mild and efficient method for chemoselective silylation of alcohols using hexamethyldisilazane in the presence of silica chloride". . p. 1567 - 1570. Retrieved 2003.
• 2、 Narsaiah, Akkirala Venkat. "Lanthanum trichloride: An efficient catalyst for the silylation of hydroxyl groups by activating hexamethyldisilazane (HMDS)". . p. 3614 - 3618. Retrieved 2007.
• 3、 Shirini, Farhad,Abedini, Masoumeh,Mahmoodi, Nosratollah,Biglari, Mohammad,Safarpoor Nikoo Langrudi, Mohaddeseh. "Introduction of a New Ionic Liquid Catalyst for the Trimethylsilyl and Tetrahydropyranyl Protection of Alcohols". . p. 1912 - 1921. Retrieved 2015.
• 4、 Khodaei, Mohammad M.,Khosropour, Ahmad R.,Abbasi, Jamshide. "A novel and highly efficient method for the direct conversion of aryl aldehyde bisulfite adducts to their aryl trimethylsilyl ethers in a one-pot manner catalyzed by montmorillonite K-10". . p. 93 - 97. Retrieved 2006.
• 5、 Karimi,Golshani. "Mild and highly efficient method for the silylation of alcohols using hexamethyldisilazane catalyzed by iodine under nearly neutral reaction conditions". . p. 7228 - 7230. Retrieved 2000.
• 6、 Ghorbani-Vaghei, Ramin,Zolfigol, Mohammad Ali,Chegeny, Mahdieh,Veisi, Hojat. "Poly(N-bromobenzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, and thiols using hexamethyldisilazane". . p. 4505 - 4508. Retrieved 2006.
• 7、 Mojtahedi, Mohammad M.,Abbasi, Hassan,Abaee, M. Saeed. "A novel efficient method for the silylation of alcohols using hexamethyldisilazane in an ionic liquid". . p. 1541 - 1544. Retrieved 2006.
• 8、 Mashhadinezhad, Maryam,Shirini, Farhad,Mamaghani, Manouchehr. "Nanoporous Na+-montmorillonite perchloric acid as an efficient and recyclable catalyst for the chemoselective protection of hydroxyl groups". . p. 2099 - 2107. Retrieved 2019/01/03.
• 9、 Zeynizadeh, Behzad,Sorkhabi, Serve. "Fast and efficient method for Silylation of alcohols and phenols with HMDS in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides". . p. 127 - 135. Retrieved 2018/02/06.