2-[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]ethan-1-ol

Base Information

• Chemical Name: 2-[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]ethan-1-ol
• CAS No.: 200880-27-9
• Molecular Formula: C17H23NO2
• Molecular Weight: 273.37000
• DSSTox Substance ID: DTXSID80578797
• Nikkaji Number: J912.514K
• Wikidata: Q82469119
• Mol file: 200880-27-9.mol

Synonyms:200880-27-9;2-[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]ethan-1-ol;SCHEMBL4804630;DTXSID80578797

Chemical Property of 2-[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]ethan-1-ol

Chemical Property:

• PSA: 45.25000
• LogP: 3.29070
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 273.172878976
• Heavy Atom Count: 20
• Complexity: 335

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C2C(=CC=C1)C3=C(N2)C(OCC3)(CC)CCO
• Isomeric SMILES: CCC1=C2C(=CC=C1)C3=C(N2)[C@@](OCC3)(CC)CCO

Technology Process of 2-[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]ethan-1-ol

There total 2 articles about 2-[(1R)-1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl]ethan-1-ol 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:

vinyl benzoate (769-78-8,24991-32-0) + (+/-)-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)ethanol (200880-25-7) → C24H27NO3 (1104730-05-3) + (1S)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanol (200880-29-1) + (1R)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanol (200880-27-9)

Guidance literature:

With Lipase A₁₂ derived from Apergillus niger; In di-isopropyl ether; at 35 ℃; for 240h; optical yield given as %ee; Resolution of racemate; Inert atmosphere; Enzymatic reaction;

DOI:10.3987/COM-08-S(N)118

Reference yield:

vinyl benzoate (769-78-8,24991-32-0) + (+/-)-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)ethanol (200880-25-7) → C24H27NO3 (1104730-05-3) + C24H27NO3 + (1S)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanol (200880-29-1) + (1R)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanol (200880-27-9)

Guidance literature:

With Lipase R derived from Penicillium roqueforti; In di-isopropyl ether; at 35 ℃; for 96h; optical yield given as %ee; Resolution of racemate; Inert atmosphere; Enzymatic reaction;

DOI:10.3987/COM-08-S(N)118

Reference yield: 78.0%

4-chlorobenzoyl chloride (586-75-4) + (1R)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanol (200880-27-9) → 4-Bromo-benzoic acid 2-((R)-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethyl ester

Guidance literature:

With triethylamine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(97)10242-3

upstream raw materials:

vinyl benzoate

(+/-)-2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)ethanol