2-[(Diphenylmethylene)amino]-4-methyl-4-pentenoic acid ethyl ester

Base Information

• Chemical Name: 2-[(Diphenylmethylene)amino]-4-methyl-4-pentenoic acid ethyl ester
• CAS No.: 80741-44-2
• Molecular Formula: C21H23NO2
• Molecular Weight: 321.419
• Mol file: 80741-44-2.mol

Synonyms:ethyl 2-[(diphenylmethylene)amino]-4-methylpent-4-enoate;2-(Benzhydrylidene-amino)-4-methyl-pent-4-enoic acid ethyl ester;ethyl (2RS)-2-Diphenylmethylenamino-4-methyl-4-pentenoate;

Chemical Property of 2-[(Diphenylmethylene)amino]-4-methyl-4-pentenoic acid ethyl ester

Chemical Property:

• Boiling Point: 395.5±42.0 °C(Predicted)
• PKA: 2.42±0.50(Predicted)
• PSA: 38.66000
• Density: 1.00
• LogP: 4.42190

Purity/Quality:

98% ^*data from raw suppliers

4-Pentenoicacid,2-[(diphenylmethylene)amino]-4-methyl-,ethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(Diphenylmethylene)amino]-4-methyl-4-pentenoic acid ethyl ester

There total 4 articles about 2-[(Diphenylmethylene)amino]-4-methyl-4-pentenoic acid ethyl ester 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: 91.0%

2-methylprop-1-enyl chloride (513-37-1) + ethyl N-diphenylmethylene glycine (69555-14-2) → ethyl 2-<(diphenylmethylene)amino>-4-methyl-(+/-)-4-pentenoate (80741-44-2)

Guidance literature:

ethyl N-diphenylmethylene glycine; With sodium t-butanolate; In N,N-dimethyl-formamide; at 5 ℃; for 0.5h; Inert atmosphere;

2-methylprop-1-enyl chloride; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h; Inert atmosphere;

Reference yield: 91.0%

ethyl N-diphenylmethylene glycine (69555-14-2) + 3-Chloro-2-methylpropene (563-47-3) → ethyl 2-<(diphenylmethylene)amino>-4-methyl-(+/-)-4-pentenoate (80741-44-2)

Guidance literature:

ethyl N-diphenylmethylene glycine; With sodium t-butanolate; In N,N-dimethyl-formamide; for 0.5h; Cooling with ice;

3-Chloro-2-methylpropene; In N,N-dimethyl-formamide;

Reference yield: 16.0%

2-methallyltrimethylsilane (18292-38-1) + ethyl 2-acetoxy-2-diphenylmethyleneaminoacetate (97611-55-7) → ethyl 2-<(diphenylmethylene)amino>-4-methyl-(+/-)-4-pentenoate (80741-44-2)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1016/S0040-4020(01)86045-2

upstream raw materials:

2-methallyltrimethylsilane

ethyl 2-acetoxy-2-diphenylmethyleneaminoacetate

ethyl N-diphenylmethylene glycine

2-methylprop-1-enyl chloride

Downstream raw materials:

ethyl (2RS)-2-amino-4-methyl-4-pentenoate

ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate

ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt

ClPt(C6H4(Ph)C=NCH(COOEt)CH2C(Me)=CH2-C,N,η2-C,C)

Refernces

• 1、 -. "PROCESS FOR PREPARING FLUOROLEUCINE ALKYL ESTERS". Page/Page column 7. . Retrieved 2013/10/21.
• 2、 O'Donell, Martin J.,Benett, William D.. "THE SYNTHESIS OF AMINO ACIDS BY REACTION OF AN ELECTROPHILIC GLYCINE CATION EQUIVALENT WITH NEUTRAL CARBON NUCLEOPHILES". . p. 5389 - 5402. Retrieved 2007/10/02.