(E)-1,5-diphenyl-3-(2-phenylethynyl)pent-1-en-4-yn-3-ol

Base Information

• Chemical Name: (E)-1,5-diphenyl-3-(2-phenylethynyl)pent-1-en-4-yn-3-ol
• CAS No.: 5394-80-9
• Molecular Formula: C25H18O
• Molecular Weight: 334.4098
• NSC Number: 800
• Nikkaji Number: J3.267.573E
• Mol file: 5394-80-9.mol

Synonyms:NSC800;(E)-1,5-diphenyl-3-(2-phenylethynyl)pent-1-en-4-yn-3-ol;NSC-800;5394-80-9;3-Styryl-1,5-diphenyl-1,4-pentadiyne-3-ol;A832879

Chemical Property of (E)-1,5-diphenyl-3-(2-phenylethynyl)pent-1-en-4-yn-3-ol

Chemical Property:

• Vapor Pressure: 1.31E-12mmHg at 25°C
• Boiling Point: 542.7°Cat760mmHg
• Flash Point: 243.4°C
• Density: 1.18g/cm³
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 334.135765193
• Heavy Atom Count: 26
• Complexity: 545

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(C#CC2=CC=CC=C2)(C#CC3=CC=CC=C3)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C(C#CC2=CC=CC=C2)(C#CC3=CC=CC=C3)O

Technology Process of (E)-1,5-diphenyl-3-(2-phenylethynyl)pent-1-en-4-yn-3-ol

There total 13 articles about (E)-1,5-diphenyl-3-(2-phenylethynyl)pent-1-en-4-yn-3-ol 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: 25.0%

phenylacetylene (536-74-3) + Cinnamoyl chloride (102-92-1,17082-09-6) → (E)-1,5-diphenyl-1-penten-4-yn-3-one (37845-36-6) + (E)-1,5-diphenyl-3-(phenylethynyl)pent-1-en-4-yn-3-ol (5394-80-9)

Guidance literature:

With n-butyllithium; cerium(III) chloride; In tetrahydrofuran; at 80 ℃; for 4h;

Reference yield: 23.0%

ethyl 3-phenyl-2-propenoate (103-36-6) + phenylacetylene (536-74-3) → 1,5-diphenyl-3-(phenylethynyl)pent-1-en-4-yn-3-ol (5394-80-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; water; Cooling with ice;

DOI:10.1016/j.tet.2013.10.007

Reference yield:

cinnamic anhydride (21947-71-7) → (E)-1,5-diphenyl-3-(phenylethynyl)pent-1-en-4-yn-3-ol (5394-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene

2: diethyl ether

With diethyl ether; benzene;

DOI:10.1021/ja01197a057

upstream raw materials:

diethyl ether

(E)-1,5-diphenyl-1-penten-4-yn-3-one

(phenylethynyl)sodium

lithium phenylacetylide

Downstream raw materials:

C₃₀H₂₅NO₂S

3-phenethyl-1,5-diphenyl-pentan-3-ol

Refernces

• 1、 Kim, Bo Ram,Lee, Hyung-Geun,Kang, Seung-Beom,Jung, Kwang-Ju,Sung, Gi Hyeon,Kim, Jeum-Jong,Lee, Sang-Gyeong,Yoon, Yong-Jin. "Synthesis of β-ketonitriles, α,β-alkynones and biscabinols from esters using tert-butoxide-assisted C(=O)-C (i.e., acyl-C) coupling under ambient conditions". . p. 10331 - 10336. Retrieved 2013/11/19.