2-Phenyl-hex-2-enenitrile

Base Information

• Chemical Name: 2-Phenyl-hex-2-enenitrile
• CAS No.: 130786-09-3
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.242
• European Community (EC) Number: 482-160-5,640-097-2
• DSSTox Substance ID: DTXSID50893843
• Nikkaji Number: J3.568.109D
• Wikidata: Q81982729
• Mol file: 130786-09-3.mol

Synonyms:2-Phenyl-hex-2-enenitrile;130786-09-3;SCHEMBL3174317;SCHEMBL3174321;(Z)-2-Phenyl-2-hexenenitrile;DTXSID50893843;(alpha Z)-alpha-Butylidenebenzeneacetonitrile;J3.568.109D;Benzeneacetonitrile, .alpha.-butylidene-, (.alpha.Z)-

Chemical Property of 2-Phenyl-hex-2-enenitrile

Chemical Property:

• Density: 0.93[at 20℃]
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 171.104799419
• Heavy Atom Count: 13
• Complexity: 213

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCC=C(C#N)C1=CC=CC=C1
• Isomeric SMILES: CCC/C=C(\C#N)/C1=CC=CC=C1

Technology Process of 2-Phenyl-hex-2-enenitrile

There total 3 articles about 2-Phenyl-hex-2-enenitrile 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: 97.0%

phenylacetonitrile (140-29-4) + butyraldehyde (123-72-8) → (Z)-2-phenyl-2-hexenenitrile (130786-09-3)

Guidance literature:

With dihydridotetrakis(triphenylphosphine)ruthenium; 1,3-bis-(diphenylphosphino)propane; In tetrahydrofuran; at 25 ℃; for 24h;

DOI:10.1021/ja00155a008

Reference yield:

pentanal (110-62-3) + phenylacetonitrile (140-29-4) → (E)-2-phenylhex-2-enenitrile (118745-27-0) + (Z)-2-phenyl-2-hexenenitrile (130786-09-3)

Guidance literature:

With N-methyl-N-trimethylsilylacetamide; In neat (no solvent); at 60 ℃; for 24h; Overall yield = 64 %; Overall yield = 55 mg; diastereoselective reaction;

DOI:10.1021/acs.orglett.6b01121

Reference yield:

phenylacetonitrile (140-29-4) + butyraldehyde (123-72-8) → (Z)-2-phenyl-2-hexenenitrile (130786-09-3) + erythro-2-phenyl-3-hydroxyhexanenitrile + threo-2-phenyl-3-hydroxyhexanenitrile

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

upstream raw materials:

phenylacetonitrile

butyraldehyde

pentanal

Refernces

• 1、 Murahashi, Shun-Ichi,Take, Kazuhiko,Naota, Takeshi,Takaya, Hikaru. "Aldol and Michael reactions of nitriles catalyzed by cyclopentadienyl- ruthenium enolate complexes". . p. 1016 - 1018. Retrieved 2007/10/03.
• 2、 Kasatkin, A. N.,Biktimirov, R. Kh.,Tolstikov, G. A.,Nikonenko, A. G.. "REACTIONS OF TITANIUM DERIVATIVES OF CERTAIN CH ACIDS WITH CARBONYL COMPOUNDS. II. ALDOL CONDENSATIONS WITH TITANIUM DERIVATIVES OF BENZYL CYANIDE, ISOPROPYL PHENYLACETATE, AND PHENYL BENZYL AND ETHYL BENZYL KETONES". . p. 1037 - 1045. Retrieved 2007/10/02.