Dehydromonocrotaline

Base Information

• Chemical Name: Dehydromonocrotaline
• CAS No.: 23291-96-5
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.346
• UNII: 1HW8C6SVG7
• DSSTox Substance ID: DTXSID80177860
• Nikkaji Number: J54.265B
• Mol file: 23291-96-5.mol

Synonyms:dehydromonocrotaline;monocrotaline pyrrole

Chemical Property of Dehydromonocrotaline

Chemical Property:

• Vapor Pressure: 3.06E-13mmHg at 25°C
• Melting Point: 30-33°C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 557°Cat760mmHg
• PKA: 12.22±0.60(Predicted)
• Flash Point: 290.6°C
• PSA: 97.99000
• Density: 1.43g/cm³
• LogP: 0.67100
• Storage Temp.: -86°C Freezer, Under Inert Atmosphere
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 323.13688739
• Heavy Atom Count: 23
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

DehydroMonocrotaline,90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)OC2CCN3C2=C(COC(=O)C(C1(C)O)(C)O)C=C3
• Isomeric SMILES: C[C@H]1C(=O)O[C@@H]2CCN3C2=C(COC(=O)[C@]([C@]1(C)O)(C)O)C=C3
• Uses: A metabolite of the potent hepatotoxin Monocrotaline.

Technology Process of Dehydromonocrotaline

There total 5 articles about Dehydromonocrotaline 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: 80.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → Monocrotalic acid (26543-09-9) + monocrotaline pyrrole (23291-96-5) + 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-(7-methoxy-6,7-dihydro-5H-pyrrolizin-1-ylmethyl)-5-methyl-1H-pyrimidine-2,4-dione (133787-49-2) + 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-(7-hydroxymethyl-2,3-dihydro-1H-pyrrolizin-1-ylmethyl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 25 ℃; for 5h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)92122-1

Reference yield:

monocrotaline (315-22-0) → monocrotaline pyrrole (23291-96-5)

Guidance literature:

monocrotaline; With chloranil; In chloroform; at 20 ℃;

With sodium tetrahydroborate; potassium hydroxide; In chloroform;

DOI:10.1016/j.cbi.2009.10.001

Reference yield:

monocrotaline (315-22-0,83114-75-4,109525-74-8,146143-26-2) → monocrotaline pyrrole (23291-96-5)

Guidance literature:

With dihydrogen peroxide; acetic anhydride; Multistep reaction; 1.) methanol, 2.) CHCl₃, 30 min;

DOI:10.1021/jo00226a027

upstream raw materials:

monocrotaline

thymidine

monocrotaline

retronecine

Downstream raw materials:

Monocrotalic acid

dehydroretronecine dimethyl ether

C₁₉H₂₄N₆O₅

1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-3-(7-methoxy-6,7-dihydro-5H-pyrrolizin-1-ylmethyl)-3,4-dihydro-1H-pyrimidin-2-one