(1E,3Z)-1,4-Diphenyl-1,3-butadiene

Base Information

• Chemical Name: (1E,3Z)-1,4-Diphenyl-1,3-butadiene
• CAS No.: 5808-05-9
• Molecular Formula: C16H14
• Molecular Weight: 206.287
• NSC Number: 122702
• UNII: 629840Z2MG
• Wikidata: Q27263464
• Mol file: 5808-05-9.mol

Synonyms:(1E,3Z)-1,4-Diphenyl-1,3-butadiene;cis,trans-1,4-Diphenylbutadiene;(E,Z)-1,4-Diphenyl-1,3-butadiene;629840Z2MG;cis,trans-1,4-Diphenyl-1,3-butadiene;1,3-Butadiene, 1,4-diphenyl-, (E,Z)-;1,4-Diphenyl-1,3-butadiene, (1E,3Z)-;UNII-629840Z2MG;1,4-Diphenyl-1,3-butadiene (E,Z)-form [MI];Benzene, 1,1'-(1E,3Z)-1,3-butadiene-1,4-diylbis-;5808-05-9;NSC122702;NSC-122702;trans,cis-1,4-diphenyl-1,3-butadiene;Benzene,1'-(1,3-butadiene-1,4-diyl)bis-;Q27263464;1,4-DIPHENYL-1,3-BUTADIENE (1E,3Z)-FORM [MI]

Chemical Property of (1E,3Z)-1,4-Diphenyl-1,3-butadiene

Chemical Property:

• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 206.109550447
• Heavy Atom Count: 16
• Complexity: 198

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC=CC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C=C\C2=CC=CC=C2

Technology Process of (1E,3Z)-1,4-Diphenyl-1,3-butadiene

There total 99 articles about (1E,3Z)-1,4-Diphenyl-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: 83.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → trans,trans-1,4-Diphenyl-1,3-butadiene (886-65-7,538-81-8) + (1Z,3E)-1,4-diphenylbuta-1,3-diene (5808-05-9)

Guidance literature:

With (^iPr₄PCP)Ir(C₂H₄); at 150 ℃; for 72h; Reagent/catalyst; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.7b03433

Reference yield: 79.0%

[(E)-2-bromoethenyl]benzene (588-72-7,1340-14-3) + 4-trifluoromethylphenylboronic acid (128796-39-4) → trans,trans-1,4-Diphenyl-1,3-butadiene (886-65-7,538-81-8) + (1Z,3E)-1,4-diphenylbuta-1,3-diene (5808-05-9) + (E)-4-trifluoromethylstilbene (1149-56-0)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; water; potassium carbonate; In toluene; at 20 ℃; for 24h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1246/bcsj.82.1292

Reference yield: 76.0%

(E)-3-phenylpropenal (14371-10-9) + (E)-N′-benzylidene-4-methylbenzenesulfonohydrazide (1666-17-7) → trans,trans-1,4-Diphenyl-1,3-butadiene (886-65-7,538-81-8) + (1Z,3E)-1,4-diphenylbuta-1,3-diene (5808-05-9)

Guidance literature:

(E)-N′-benzylidene-4-methylbenzenesulfonohydrazide; With potassium tert-butylate; In toluene; at 0 - 20 ℃; for 1h;

(E)-3-phenylpropenal; With 5,10,15,20-tetraphenyl porphyrinato iron hydroxide; Aliquat 336; phosphorous acid trimethyl ester; In toluene; at 40 ℃; for 48h;

DOI:10.1021/ja029573x

upstream raw materials:

trans,trans-1,4-Diphenyl-1,3-butadiene

1,4-diphenyl-1,3-butadiyne

(Z)-β-bromostyrene

(E)-2-(2'-phenylethenyl)-1,3,2-benzodioxaborole

Downstream raw materials:

trans,trans-1,4-Diphenyl-1,3-butadiene

cis-N-p-toluenesulfonyl-2,5-diphenyl-3-pyrroline

C₁₆H₁₄

Refernces

• 1、 Zhuang, Xuewen,Chen, Jia-Yi,Yang, Zhuoyi,Jia, Mengjing,Wu, Chengjuan,Liao, Rong-Zhen,Tung, Chen-Ho,Wang, Wenguang. "Sequential Transformation of Terminal Alkynes to 1,3-Dienes by a Cooperative Cobalt Pyridonate Catalyst". supporting information. p. 3752 - 3759. Retrieved 2019/11/13.
• 2、 Thiel, Niklas O.,Kemper, Sebastian,Teichert, Johannes F.. "Copper(I)-catalyzed stereoselective hydrogenation of 1,3-diynes and enynes". . p. 5023 - 5028. Retrieved 2017/07/27.