Phenylpentadien

Base Information

• Chemical Name: Phenylpentadien
• CAS No.: 1608-27-1
• Molecular Formula: C11H12
• Molecular Weight: 144.216
• DSSTox Substance ID: DTXSID001312175
• Mol file: 1608-27-1.mol

Synonyms:Phenylpentadien;1,3-Pentadien-1-ylbenzene;DTXSID001312175

Chemical Property of Phenylpentadien

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 144.093900383
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=CC1=CC=CC=C1

Technology Process of Phenylpentadien

There total 84 articles about Phenylpentadien 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: 83.0%

ethene (74-85-1) + (Z)-(3-methoxyprop-1-en-1-yl)benzene (16277-67-1,22688-03-5,24808-73-9) → (1E,3E)-1-phenyl-1,3-pentadiene (3909-96-4) + (1E)-1,4-pentadienylbenzene (55666-17-6) + (Z)-1-phenyl-4-methyl-1,3-butadiene (1608-27-1,3909-96-4,39491-55-9,39491-56-0,66597-12-4,66597-13-5,7642-05-9)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tris(o-methoxyphenyl)phosphine; triethylsilyl trifluoromethyl sulfonate; triethylamine; In toluene; at 20 ℃; for 0.833333h; Inert atmosphere;

DOI:10.1021/ja101186p

Reference yield: 80.0%

(E)-1-phenylpent-2-enyl acetate (849590-67-6) → ((1E)-penta-1,3-dien-1-yl)benzene (1608-27-1,3909-96-4,7642-05-9,39491-55-9,39491-56-0,66597-13-5,66597-12-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; bis[1,2-bis(diphenylphosphino)ethane]palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1246/cl.2005.256

Reference yield: 79.0%

[(E)-2-bromoethenyl]benzene (588-72-7,1340-14-3) + (Z)-1-propenyllithium (6524-17-0,29283-76-9,6386-72-7) → (Z)-1-phenyl-4-methyl-1,3-butadiene (1608-27-1,3909-96-4,39491-55-9,39491-56-0,66597-12-4,66597-13-5,7642-05-9)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In toluene; at 20 ℃; for 1h; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1039/c4sc03117b

upstream raw materials:

1-phenyl-pent-1-en-3-ol

diethyl ether

4-nitro-benzoyl chloride

styrene

Downstream raw materials:

3-methyl-6-phenyl-cyclohex-4-ene-1,2-dicarboxylic acid-anhydride

3-methyl-6-phenyl-3,6-dihydro-pyridazine-1,2-dicarboxylic acid diethyl ester

2-phenyl-3-(1-propenyl)oxirane

agropyrene

Refernces

• 1、 Morisaki, Yasuhiro,Kondo, Teruyuki,Mitsudo, Take-Aki. "A new route to cyclopentenones via ruthenium-catalyzed carbonylative cyclization of allylic carbonates with alkenes". . p. 949 - 952. Retrieved 2000.
• 2、 Zapata, Antonio J.,Ruiz, Jacqueline. "Palladium-catalyzed coupling reactions of functionalized styryl bromides with 1-propenyltributyltin". . p. C6 - C8. Retrieved 1994.
• 3、 Wang, Chengdong,Guo, Yingjie,Wang, Xiaoming,Wang, Zheng,Ding, Kuiling. "Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides". supporting information. p. 15903 - 15907. Retrieved 2021/10/07.
• 4、 Dong, Dongfang,Zhang, Qinglong,Zi, Weiwei. "Palladium-Catalyzed Regio- A nd Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity". supporting information. p. 15860 - 15869. Retrieved 2020/10/18.