Crotanecine

Base Information

• Chemical Name: Crotanecine
• CAS No.: 5096-50-4
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.1937
• NSC Number: 697380
• DSSTox Substance ID: DTXSID00965226
• Nikkaji Number: J13.426K
• Wikidata: Q27106247
• Mol file: 5096-50-4.mol

Synonyms:Crotanecine;5096-50-4;(1s,2r,8r)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1h-pyrrolizine-1,2-diol;NSC697380;NSC-697380;C10284;7-(Hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizine-1,2-diol;CHEBI:3925;DTXSID00965226;AKOS040734818;Q27106247;(1S,2R,7aR)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizine-1,2-diol

Chemical Property of Crotanecine

Chemical Property:

• Vapor Pressure: 5.73E-07mmHg at 25°C
• Boiling Point: 369.6°Cat760mmHg
• Flash Point: 227.9°C
• PSA: 63.93000
• Density: 1.45g/cm³
• LogP: -1.73740
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 171.08954328
• Heavy Atom Count: 12
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

Crotanecine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C=C(C2N1CC(C2O)O)CO
• Isomeric SMILES: C1C=C([C@H]2N1C[C@H]([C@H]2O)O)CO

Technology Process of Crotanecine

There total 22 articles about Crotanecine 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: 76.0%

(6R,7S,7aR)-6,7-Diacetoxy-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid ethyl ester (95687-36-8) → (+)-crotanecine (5096-50-4)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 - 20 ℃;

Reference yield: 74.0%

anacrotine → (+)-crotanecine (5096-50-4)

Guidance literature:

With sodium hydroxide; for 2.5h; Heating;

DOI:10.1021/ja963084d

Reference yield:

Methanesulfonic acid (2aR,3R,7R,7aS,7bR)-7-(dimethyl-phenyl-silanyl)-2-methoxy-4-oxo-octahydro-furo[2,3,4-gh]pyrrolizin-3-yl ester → (+)-crotanecine (5096-50-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / KBr, NaOAc, HOOAc / acetic acid / 3 h / Ambient temperature

2: aq. CF₃CO₂H / 40 - 60 °C / other temperature

3: 1.) BH₃, 2.) Et₃N / 1.) THF, 72 deg C, 4 h, 2.) MeOH, 120-130 deg C, 5 h

With peracetic acid; borane; sodium acetate; triethylamine; trifluoroacetic acid; potassium bromide; In acetic acid;

DOI:10.1021/ja963084d

upstream raw materials:

(3aR,8aR,8bS)-2,2-Dimethyl-3a,6,8a,8b-tetrahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine-8-carboxylic acid methyl ester

(6R,7S,7aR)-6,7-Diacetoxy-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid ethyl ester

(1S,5R,8R)-ethyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate

(1S,5R,8R)-ethyl 8-(dimethyl-t-butylsiloxy)-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate

Refernces

• 1、 Bennett III,Cha. "An enantioselective synthesis of (+)-crotanecine by an intramolecular azide 1,3-dipolar cycloaddition". . p. 5437 - 5440. Retrieved 2007/10/02.