1-METHYL-3-PHENYLPROPYLISOCYANIDE

Base Information

• Chemical Name: 1-METHYL-3-PHENYLPROPYLISOCYANIDE
• CAS No.: 910213-03-5
• Molecular Formula: C₁₁H₁₃N
• Molecular Weight: 159.231
• Mol file: 910213-03-5.mol

Synonyms:(S)-4-phenylbutan-2-yl isocyanide

Chemical Property of 1-METHYL-3-PHENYLPROPYLISOCYANIDE

Chemical Property:

Purity/Quality:

1-METHYL-3-PHENYLPROPYLISOCYANIDE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-METHYL-3-PHENYLPROPYLISOCYANIDE

There total 2 articles about 1-METHYL-3-PHENYLPROPYLISOCYANIDE 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: 71.0%

(R)-1-methyl-3-phenylpropyl diphenylphosphinite (866483-65-0) + diethyl cyanophosphonate (2942-58-7) → (S)-4-phenylbutan-2-yl isocyanide (910213-03-5)

Guidance literature:

With 2,6-dimethyl-1,4-benzoquinone; zinc(II) oxide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1246/bcsj.79.1106

Reference yield:

(R)-4-phenyl-2-butanol (2344-70-9,14786-43-7,22148-86-3,39516-03-5) → (S)-4-phenylbutan-2-yl isocyanide (910213-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 20 °C

2: 71 percent / 2,6-dimethyl-1,4-benzoquinone; zinc oxide / CH₂Cl₂ / 24 h / 20 °C

With dmap; 2,6-dimethyl-1,4-benzoquinone; triethylamine; zinc(II) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.79.1106

Reference yield: 32.0%

(S)-4-phenylbutan-2-yl isocyanide (910213-03-5) + 3-pyridinecarboxaldehyde (500-22-1) + dichloro-acetic acid (79-43-6) + 4-phenylalanine (92-67-1) → N-([1,1'-biphenyl]-4-yl)-2,2-dichloro-N-((R)-2-oxo-2-(((S)-4-phenylbutan-2-yl)amino)-1-(pyridin-3-yl)ethyl)acetamide + N-([1,1'-biphenyl]-4-yl)-2,2-dichloro-N-((S)-2-oxo-2-(((S)-4-phenylbutan-2-yl)amino)-1-(pyridin-3-yl)ethyl)acetamide

Guidance literature:

3-pyridinecarboxaldehyde; 4-phenylalanine; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

(S)-4-phenylbutan-2-yl isocyanide; dichloro-acetic acid; In methanol; at 20 ℃; Inert atmosphere;

With Lux5 μM i-Amylose-3 column; Resolution of racemate;

DOI:10.1021/jacs.1c08060

upstream raw materials:

(R)-1-methyl-3-phenylpropyl diphenylphosphinite

diethyl cyanophosphonate

(R)-4-phenyl-2-butanol

Downstream raw materials:

(S)-1-methyl-3-phenylpropylamine

Refernces

• 1、 Masutani, Kouta,Minowa, Tomofumi,Mukaiyama, Teruaki. "Selective synthesis of isocyanides from secondary alcohols by a new type of oxidation-reduction condensation". . p. 1124 - 1125. Retrieved 2007/10/03.