Preussin

Base Information

• Chemical Name: Preussin
• CAS No.: 119463-16-0
• Molecular Formula: C₂₁H₃₅NO
• Molecular Weight: 317.515
• DSSTox Substance ID: DTXSID00922975
• Nikkaji Number: J410.832I
• Wikidata: Q82896799
• Mol file: 119463-16-0.mol

Synonyms:(+)-preussin;L 657398;L-657,398;preussin;preussin, (+)-isomer

Chemical Property of Preussin

Chemical Property:

• Vapor Pressure: 3.1E-08mmHg at 25°C
• Boiling Point: 432.1°Cat760mmHg
• PKA: 14.95±0.60(Predicted)
• Flash Point: 11.1°C
• PSA: 23.47000
• Density: 0.967g/cm³
• LogP: 4.74130
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 317.271864740
• Heavy Atom Count: 23
• Complexity: 300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC1CC(C(N1C)CC2=CC=CC=C2)O

Technology Process of Preussin

There total 310 articles about Preussin 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: 100.0%

(2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol (131013-30-4) → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1021/jo00003a040

Reference yield: 98.0%

(2S,3S,5S)-2-Benzyl-1-methyl-5-((E)-non-1-enyl)-pyrrolidin-3-ol → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr;

DOI:10.1055/s-1997-1347

Reference yield: 94.0%

(2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine (159154-02-6) → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2.5h; Heating;

DOI:10.1021/ja00104a005

upstream raw materials:

(2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol

tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate

(S)-2-Benzyl-5-nonyl-3-oxo-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

(2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine

Refernces

• 1、 Hausherr, Arndt,Siemeister, Gerhard,Reissig, Hans-Ulrich. "Alkoxyallene-based syntheses of preussin and its analogs and their cytotoxicity". . p. 122 - 134. Retrieved 2019.
• 2、 Si, Chang-Mei,Shao, Lu-Ping,Mao, Zhuo-Ya,Zhou, Wen,Wei, Bang-Guo. "An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin". . p. 649 - 661. Retrieved 2017/01/25.