uleine

Base Information

• Chemical Name: uleine
• CAS No.: 517-81-7
• Molecular Formula: C18H22N2
• Molecular Weight: 266.3807
• Mol file: 517-81-7.mol

Synonyms:ulein;1-methylene-dasycarpidane;uleine;

Chemical Property of uleine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 123 - 125 °C
• Boiling Point: 437.6°Cat760mmHg
• Flash Point: 218.5°C
• PSA: 19.03000
• Density: 1.14g/cm³
• LogP: 4.15160

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: An Aspidosperma alkaloid, this base occurs in several members of this species and particularly in A. ulei. It forms colourless crystals having the double melting point given above. It is slightly dextrorotatory with [α]25D + 11.5° (CHCI3 ) and gives an ultraviolet spectrum having a broad absorption maximum at 307-8 Mu.1 and a second maximum at 316 IT1J.1. The hydrochloride is crystalline with m.p. 241-2°C and the tnethiodide has m.p. 204-6°C. Oxidation with KMn04 yields formaldehyde indicative of an exocyc1ic methylene group.

Technology Process of uleine

There total 91 articles about uleine 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: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + noruleine → 20-epiuleine (517-81-7,17463-46-6,19775-50-9,19775-51-0)

Guidance literature:

With sodium cyanoborohydride; In water; acetonitrile; at 20 ℃; for 0.66h;

DOI:10.1021/acs.joc.6b00240

Reference yield: 85.0%

1,13-Dihydroulein-Nb-oxid (99612-57-4) → Ulein (517-81-7,17463-46-6,19775-50-9,19775-51-0)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; for 0.0333333h;

Reference yield: 83.0%

methyllithium (917-54-4) + (+)-dasycarpidone (2825-08-3,16530-89-5,18688-38-5,18700-27-1) → (+)-uleine (517-81-7,17463-46-6,19775-50-9,19775-51-0)

Guidance literature:

methyllithium; (+)-dasycarpidone; In tetrahydrofuran; at 0 ℃;

With trifluoroacetic acid; In dichloromethane; at 23 ℃; for 0.25h; enantioselective reaction;

DOI:10.1002/hlca.202100088

upstream raw materials:

cis-1,4-diacetoxy-2-cyclopentene

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate

C₁₆H₂₀N₂

Downstream raw materials:

1,13-Dihydro-ulein

Ulein-N^b-oxid

Refernces

• 1、 Delayre, Bastien,Fung, Cédric,Wang, Qian,Zhu, Jieping. "Enantioselective Total Synthesis of (+)-Nordasycarpidone, (+)-Dasycarpidone, and (+)-Uleine". . . Retrieved 2021/07/12.
• 2、 Sakaguchi, Taku,Kobayashi, Shohei,Katsumura, Shigeo. "Total synthesis of (-)-20-epiuleine via stereocontrolled one-pot asymmetric azaelectrocyclization followed by novel 1,4-addition reaction". experimental part. p. 257 - 264. Retrieved 2011/02/24.