Julocrotine

Base Information

• Chemical Name: Julocrotine
• CAS No.: 492-87-5
• Molecular Formula: C18H24N2O3
• Molecular Weight: 316.3948
• Mol file: 492-87-5.mol

Synonyms:N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide;N-((S)-2-methyl-butyryl)-L-glutamic acid phenethylimide;julocrotine;(S)-N-[(S)-2,6-dioxo-1-phenethylpiperidin-3-yl]-2-methylbutanamide;Julocrotin, N-α-Methyl-butyryl-glutaminsaeure-β-phenylethyl-imid;(-)-julocrotine;N-((S)-2-Methyl-butyryl)-L-glutaminsaeure-phenaethylimid;(S)-N-((S)-2,6-Dioxo-1-phenethyl-piperidin-3-yl)-2-methyl-butyramide;

Chemical Property of Julocrotine

Chemical Property:

• Vapor Pressure: 1.02E-12mmHg at 25°C
• Melting Point: 108-109°
• Boiling Point: 563.4°Cat760mmHg
• Flash Point: 294.5°C
• PSA: 66.48000
• Density: 1.15g/cm³
• LogP: 2.23780

Purity/Quality:

98% ^*data from raw suppliers

JULOCROTINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A piperidinedione alkaloid, this base occurs in the roots of Juiocroton montevi_x0002_densis L. It has [α] D - 50° (MeOH) or - 9° (CHC13). The alkaloid sublimes at 165°CjO.25 mm.

Technology Process of Julocrotine

There total 16 articles about Julocrotine 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: 96.0%

(S)-N-((S)-2,6-dioxo-1-phenethylpiperidin-3-yl)-N-((R)-1-(4-methoxyphenyl)ethyl)-2-methylbutanamide → N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide (492-87-5)

Guidance literature:

(S)-N-((S)-2,6-dioxo-1-phenethylpiperidin-3-yl)-N-((R)-1-(4-methoxyphenyl)ethyl)-2-methylbutanamide; With trifluoroacetic acid; at 20 ℃; for 0.166667h;

for 24h; Reflux;

DOI:10.1002/ejoc.201801276

Reference yield:

(S)-2-Methylbutyric acid (1730-91-2) + C13H16N2O2 (1175950-31-8) → N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide (492-87-5)

Guidance literature:

With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 20 ℃; for 12h;

DOI:10.1021/np200234e

Reference yield:

C13H16N2O2 (1175950-31-8) + (S)-(+)-2-methylbutyric anhydride (84131-91-9) → N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide (492-87-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/cjoc.201180248

upstream raw materials:

(S)-2-Methylbutyric acid

C₁₃H₁₆N₂O₂

(4S)-5-oxo-4-[[(phenylmethoxy)carbonyl]amino]-5-[(2-phenylethyl)amino]pentanoic acid

L-glutamic acid

Downstream raw materials:

N²-((S)-2-methyl-butyryl)-N¹-phenethyl-L-isoglutamine

N-((S)-2-methyl-butyryl)-L-glutamic acid-1-methyl ester-5-phenethylamide

Refernces

• 1、 Silva, Luciano L.,Joussef, Antonio C.. "Synthesis of N -[(3 S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2 S)-2-methylbutanamide (( - )-julocrotine)". experimental part. p. 1531 - 1534. Retrieved 2011/08/21.
• 2、 Teng, Bo,Zheng, Jianfeng,Huang, Huiying,Huang, Peiqiang. "Enantioselective synthesis of glutarimide alkaloids cordiarimides A, B, crotonimides A, B, and julocrotine". experimental part. p. 1312 - 1318. Retrieved 2011/10/31.