2-[2-[(2S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-1H-indol-3-yl]ethanol

Base Information

• Chemical Name: 2-[2-[(2S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-1H-indol-3-yl]ethanol
• CAS No.: 482-28-0
• Molecular Formula: C19H24 N2 O
• Molecular Weight: 296.412
• European Community (EC) Number: 207-579-0
• DSSTox Substance ID: DTXSID90878432
• Mol file: 482-28-0.mol

Synonyms:cinchonamine

Chemical Property of 2-[2-[(2S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-1H-indol-3-yl]ethanol

Chemical Property:

• Vapor Pressure: 6.11E-10mmHg at 25°C
• Melting Point: 186°; mp 194°
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 477.9°Cat760mmHg
• PKA: pK in 80% methyl Cellosolve: 8.28(at 25℃)
• Flash Point: 242.8°C
• PSA: 39.26000
• Density: 1.2g/cm³
• LogP: 3.20950
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 296.188863393
• Heavy Atom Count: 22
• Complexity: 412

Purity/Quality:

99%, ^*data from raw suppliers

CINCHONAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1CN2CCC1CC2C3=C(C4=CC=CC=C4N3)CCO
• Isomeric SMILES: C=C[C@H]1CN2CCC1C[C@H]2C3=C(C4=CC=CC=C4N3)CCO

Technology Process of 2-[2-[(2S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-1H-indol-3-yl]ethanol

There total 8 articles about 2-[2-[(2S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-1H-indol-3-yl]ethanol 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:

o-toluidine (95-53-4) → (+)-cinchonamine (482-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / LiI, cyclohexene oxide / chlorotrimethylsilane / neat (no solvent) / 20 h / Heating

2: 1.) n-BuLi / 1.) hexane, 0 deg C, reflux, 6.5 h; 2.) THF, from -78 deg C up to room temp.

3: 1.) MeMgI / 1.) diethyl ether, room temp. 15 min; 2.) diethyl ether, room temp. 1 h,reflux, 2 h

With methyl magnesium iodide; n-butyllithium; cyclohexane-1,2-epoxide; lithium iodide; chloro-trimethyl-silane; In neat (no solvent);

DOI:10.1016/S0040-4020(01)90586-1

Reference yield:

quinamine (464-85-7,464-86-8,77549-88-3) → (+)-cinchonamine (482-28-0)

Guidance literature:

With lithium aluminium tetrahydride; diethyl ether; Erhitzen des Reaktionsprodukts;

DOI:10.1002/hlca.19500330124

Reference yield:

→ (+)-cinchonamine (482-28-0)

Guidance literature:

With sulfuric acid;

upstream raw materials:

quinamine

oxirane

(1S,2S,4S,5R)-2-(1H-Indol-2-yl)-5-vinyl-1-aza-bicyclo[2.2.2]octane

ethanol

Downstream raw materials:

Dihydrocinchonamin

quinamine

Refernces