(R)-Rhazinilam

Base Information

• Chemical Name: (R)-Rhazinilam
• CAS No.: 36193-36-9
• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 294.396
• DSSTox Substance ID: DTXSID90957594
• Wikipedia: Rhazinilam
• Wikidata: Q105288584
• Metabolomics Workbench ID: 46040
• Mol file: 36193-36-9.mol

Synonyms:rhazinilam;rhazinilam, (8aR*,14aR*)-(+-)-isomer

Chemical Property of (R)-Rhazinilam

Chemical Property:

• Vapor Pressure: 3.56E-11mmHg at 25°C
• Boiling Point: 526.5°Cat760mmHg
• Flash Point: 272.2°C
• Density: 1.21g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 294.173213330
• Heavy Atom Count: 22
• Complexity: 437

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC12CCCN3C1=C(C=C3)C4=CC=CC=C4NC(=O)CC2
• Description: This alkaloid is also a constituent of the leaves of Rhazya stricta and is isolated by chromatography on an alumina column followed by recrystallization from cyclohexane when it forms colourless plates. The ultraviolet spectrum shows an absorption maximum at 213 mJi and inflexions at 220 and 275 mμ

Technology Process of (R)-Rhazinilam

There total 97 articles about (R)-Rhazinilam 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%

(±)-methyl rhazinilam-5-carboxylate (52706-26-0) → (±)-rhazinilam (36193-36-9,52745-52-5,75023-11-9,1246197-08-9)

Guidance literature:

(±)-methyl rhazinilam-5-carboxylate; With sodium hydroxide; In methanol; at 50 ℃; for 0.5h;

With hydrogenchloride; In methanol; at 50 ℃; for 4h; pH=2;

DOI:10.1021/ol052033v

Reference yield: 74.0%

(±)-leuconolam → (±)-rhazinilam (36193-36-9,52745-52-5,75023-11-9,1246197-08-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; hexane; at 20 ℃; for 6h;

DOI:10.1021/ol503150c

Reference yield: 51.0%

3-[1-(2-amino-phenyl)-8-ethyl-5,6,7,8-tetrahydro-indolizin-8-yl]-propionic acid → (±)-rhazinilam (36193-36-9,52745-52-5,75023-11-9,1246197-08-9)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In tetrahydrofuran; toluene; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00859-6

upstream raw materials:

(+/-)-Rhazinilam-5-carbonsaeure

(±)-methyl rhazinilam-5-carboxylate

1-[3-(2-ethyl-5-oxo-tetrahydro-furan-2-yl)-propyl]-1H-pyrrole-2-carboxylic acid methyl ester

8-(2-carboxy-ethyl)-8-ethyl-5,6,7,8-tetrahydro-indolizine-3-carboxylic acid methyl ester

Downstream raw materials:

aspidospermidine

(±)-ter-butyl rhazinilam-N-carboxylate

Refernces

• 1、 Dagoneau, Dylan,Xu, Zhengren,Wang, Qian,Zhu, Jieping. "Enantioselective Total Syntheses of (-)-Rhazinilam, (-)-Leucomidine B, and (+)-Leuconodine F". . p. 760 - 763. Retrieved 2016/02/27.
• 2、 Su, Youla,Zhou, Haipin,Chen, Jiaxuan,Xu, Jinyi,Wu, Xiaoming,Lin, Aijun,Yao, Hequan. "Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: Application to the total synthesis of (±)-rhazinilam". . p. 4884 - 4887. Retrieved 2015/04/27.