9,11,12,13,13a,14-Hexahydrophenanthro[9,10-f]indolizine

Base Information

• Chemical Name: 9,11,12,13,13a,14-Hexahydrophenanthro[9,10-f]indolizine
• CAS No.: 7127-73-3
• Molecular Formula: C₂₀H₁₉N
• Molecular Weight: 273.378
• NSC Number: 101644
• DSSTox Substance ID: DTXSID70295385,DTXSID60864009
• Nikkaji Number: J2.300.727D
• ChEMBL ID: CHEMBL582503
• Mol file: 7127-73-3.mol

Synonyms:GNF-Pf-2936;MLS002703653;SMR001570370;7127-73-3;NSC101644;9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine;NCIOpen2_006793;CHEMBL582503;cid_265522;BDBM89216;DTXSID60864009;DTXSID70295385;9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline;NSC-101644;NCI60_000046;9,11,12,13,13a,14-hexahydrophenanthr[9,10-f]indolizine

Chemical Property of 9,11,12,13,13a,14-Hexahydrophenanthro[9,10-f]indolizine

Chemical Property:

• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 273.151749610
• Heavy Atom Count: 21
• Complexity: 391

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC3=C(CN2C1)C4=CC=CC=C4C5=CC=CC=C35

Technology Process of 9,11,12,13,13a,14-Hexahydrophenanthro[9,10-f]indolizine

There total 11 articles about 9,11,12,13,13a,14-Hexahydrophenanthro[9,10-f]indolizine 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: 92.0%

11,12,12a,13-tetrahydro-10H-9a-aza-cyclopenta[b]triphenylen-9-one (882738-83-2) → 2,3,6,7-Tetrademethoxytylophorin (7127-73-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In 1,4-dioxane; toluene; for 2h; Heating;

DOI:10.1039/b516152e

Reference yield: 63.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + tert-butyl 2-(phenanthren-9-ylmethyl)pyrrolidine-1-carboxylate → 2,3,6,7-Tetrademethoxytylophorin (7127-73-3)

Guidance literature:

formaldehyd; tert-butyl 2-(phenanthren-9-ylmethyl)pyrrolidine-1-carboxylate; With trifluoroacetic acid; In water; at 20 - 90 ℃; Inert atmosphere;

With sodium hydroxide; In water; pH=9;

DOI:10.1021/jo902114u

Reference yield:

2-(3-chloro-propyl)-2H-2-aza-triphenylen-1-one (882738-84-3) → 2,3,6,7-Tetrademethoxytylophorin (7127-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NaI / acetonitrile / 12 h / 125 °C

2: 76 percent / AIBN; n-Bu₃SnH / toluene / 6 h / Heating

3: 92 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene; dioxane / 2 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; In 1,4-dioxane; toluene; acetonitrile;

DOI:10.1039/b516152e

upstream raw materials:

N-(4-hydroxy-1-[9]phenanthrylmethyl-butyl)-formamide

toluene

trichlorophosphate

11,12,12a,13-tetrahydro-10H-9a-aza-cyclopenta[b]triphenylen-9-one

Refernces

• 1、 Rossiter, Lana M.,Slater, Meagan L.,Giessert, Rachel E.,Sakwa, Samuel A.,Herr, R. Jason. "A concise palladium-catalyzed carboamination route to (±)- tylophorine". supporting information; experimental part. p. 9554 - 9557. Retrieved 2010/03/03.