(Octahydro-indolizin-8-YL)-methanol

Base Information

• Chemical Name: (Octahydro-indolizin-8-YL)-methanol
• CAS No.: 111975-29-2
• Molecular Formula: C₉H₁₇NO
• Molecular Weight: 155.24
• DSSTox Substance ID: DTXSID60553441
• Nikkaji Number: J2.365.879H
• Wikidata: Q82434025
• Mol file: 111975-29-2.mol

Synonyms:(OCTAHYDRO-INDOLIZIN-8-YL)-METHANOL;111975-29-2;1,2,3,5,6,7,8,8a-octahydroindolizin-8-ylmethanol;(Octahydroindolizin-8-yl)methanol;DTXSID60553441;AKOS006285749

Chemical Property of (Octahydro-indolizin-8-YL)-methanol

Chemical Property:

• PSA: 23.47000
• LogP: 0.79100
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 155.131014166
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

(OCTAHYDRO-INDOLIZIN-8-YL)-METHANOL 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C2CCCN2C1)CO
• General Description: **(OCTAHYDRO-INDOLIZIN-8-YL)-METHANOL**, also known as (-)-tashiromine, is a naturally occurring indolizidine alkaloid isolated from *Maackia tashiroi*. It features a bicyclic indolizidine core with a hydroxymethyl substituent at the C-8 position, and its structure was confirmed as (5S,6R)-5-hydroxymethyl-*trans*-indolizidine (or its enantiomer) through spectral comparisons with synthetic analogs. (OCTAHYDRO-INDOLIZIN-8-YL)-METHANOL has been synthesized via concise routes, including olefin cross-metathesis and electrophile-induced ring-closure strategies, as well as enaminone-based approaches, demonstrating stereochemical control in constructing its framework.

Technology Process of (Octahydro-indolizin-8-YL)-methanol

There total 155 articles about (Octahydro-indolizin-8-YL)-methanol 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%

methyl trans-indolizidine-8-carboxylate → (+/-)-tashiromine (111975-29-2,126371-98-0,128573-77-3,130695-85-1,130695-86-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1039/b100407g

Reference yield: 95.0%

(±)-(octahydroindolizin-8-yl)methyl acetate → (+/-)-tashiromine (111975-29-2,126371-98-0,128573-77-3,130695-85-1,130695-86-2)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2018.04.067

Reference yield: 88.0%

(8R,8aS)-8-((benzyloxy)methyl)octahydroindolizine → (-)-tashiromine (111975-29-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2015.05.011

upstream raw materials:

3-(2(R)-(5-oxo-2(S)-pyrrolidinyl)-5-chlorovaleryl)-4(S)-isopropyl-1,3-thiazolidine-2-thione

(8R,8aS)-8-(2,2,6,6-Tetramethyl-piperidin-1-yloxymethyl)-octahydro-indolizine

rac-(5,6,7,8-tetrahydroindolizin-8-yl)methanol

(2S)-pentane-1,2,5-triol

Downstream raw materials:

(+/-)-tashiromine