[S,(-)]-2-Hydroxy-4-phenyl-3-butenenitrile

Base Information

• Chemical Name: [S,(-)]-2-Hydroxy-4-phenyl-3-butenenitrile
• CAS No.: 132617-10-8
• Molecular Formula: C10H9NO
• Molecular Weight: 0.00000
• Mol file: 132617-10-8.mol

Synonyms:

Chemical Property of [S,(-)]-2-Hydroxy-4-phenyl-3-butenenitrile

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-HYDROXY-4-PHENYL-3-BUTENENITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [S,(-)]-2-Hydroxy-4-phenyl-3-butenenitrile

There total 63 articles about [S,(-)]-2-Hydroxy-4-phenyl-3-butenenitrile 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%

trimethylsilyl cyanide (7677-24-9) + 3-phenyl-propenal (104-55-2) → (E)-(S)-2-Hydroxy-4-phenyl-but-3-enenitrile (132617-10-8)

Guidance literature:

With 4 A molecular sieve; dimethylaluminum chloride; Triphenylphosphine oxide; (R)-BINOLAM; In toluene; at -40 ℃; for 12h;

DOI:10.1021/ol0262338

Reference yield: 99.0%

trimethylsilyl cyanide (7677-24-9) + 3-phenyl-propenal (104-55-2) → (E)-(R)-2-Hydroxy-4-phenyl-but-3-enenitrile (132617-10-8)

Guidance literature:

With Tributylphosphine oxide; (R)-3,3'-bis(diphenylphosphinoylmethyl)-1,1'-binaphthalene-2,2'-dioxyaluminium chloride; In dichloromethane; at -40 ℃; for 40h;

DOI:10.1021/ja983895c

Reference yield: 96.0%

(E)-3-phenylpropenal (14371-10-9) + trimethylsilyl cyanide (7677-24-9) → 2-hydroxy-4-phenyl-3-butenenitrile (61912-03-6,132617-10-8) + 3-Phenylpropionic acid (501-52-0)

Guidance literature:

(E)-3-phenylpropenal; trimethylsilyl cyanide; With tris(2,4,6-trimethoxyphenyl)phosphine; In diethyl ether; at 32 ℃; for 2h;

With hydrogenchloride; In diethyl ether; water; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(02)01133-4

upstream raw materials:

potassium cyanide

3-phenyl-propenal

trimethylsilyl cyanide

(E)-3-phenylpropenal

Downstream raw materials:

(R)-2-hydroxy4-phenylbutanoic acid

(2R)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester

2-hydroxy-4-phenyl-but-3-enoic acid amide

Refernces

• 1、 Baeza, Alejandro,Casas, Jesus,Najera, Carmen,Sansano, Jose M.. "Diastereoselective and enantiospecific synthesis of γ-substituted α,β-unsaturated nitriles from O-protected allylic cyanohydrins". . p. 3837 - 3848. Retrieved 2006.
• 2、 He, Kailun,Liu, Huijun,Zhang, Xingxian,Zhou, Jing. "Highly chemoselective and efficient Strecker reaction of aldehydes with TMSCN catalyzed by MgI2 etherate under solvent-free conditions". supporting information. p. 933 - 936. Retrieved 2019/03/08.
• 3、 Meng, Fanli,Yin, Yan,Lu, Cheng,Duan, Yongbin,Zhu, Yaohua,Huang, Chen,Zhou, Yiming,Xu, Xu,Wu, Fanhong. "Design, synthesis, and in vitro evaluation of epigoitrin derivatives as neuraminidase inhibitors". . p. 2037 - 2046. Retrieved 2018/09/06.