4-(7-Methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl)phenol

Base Information

• Chemical Name: 4-(7-Methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl)phenol
• CAS No.: 26294-41-7
• Molecular Formula: C15H19NO
• Molecular Weight: 229.322
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50949157
• Mol file: 26294-41-7.mol

Synonyms:ipalbidine;ipalbidine, (S)-isomer

Chemical Property of 4-(7-Methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl)phenol

Chemical Property:

• Vapor Pressure: 2.16E-06mmHg at 25°C
• Boiling Point: 382.4°C at 760 mmHg
• Flash Point: 195.1°C
• PSA: 23.47000
• Density: 1.16g/cm³
• LogP: 2.97170
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 229.146664230
• Heavy Atom Count: 17
• Complexity: 315

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CN2CCCC2C1)C3=CC=C(C=C3)O
• Description: An indolizine alkaloid occurring in the seeds of Ipomoea alba L. (moonflower), this base yields colourless crystals and forms crystalline salts, e.g. the hydro_x0002_chloride, m.p. 104°C; picrate, m.p. 178°C and the methiodide, m.p. 206-7°C. The O-acetate is a colourless liquid, b.p. 135-7°C/l.0 mm. The structure of the alkaloid has been established from spectroscopic data.

Technology Process of 4-(7-Methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl)phenol

There total 38 articles about 4-(7-Methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl)phenol 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: 78.0%

6-(4-methoxyphenyl)-7-methyl-1,2,3,5,8,8a-hexahydroindolizine (29079-30-9) → 4-[7-methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl]phenol (26294-41-7,23506-90-3,31470-47-0)

Guidance literature:

With boron tribromide; In dichloromethane;

DOI:10.1021/jo00370a039

Reference yield:

2-(4'-hydroxyphenyl)-3-(pyrrol-1-yl)propionic acid (111751-81-6) → 4-[7-methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl]phenol (26294-41-7,23506-90-3,31470-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / N-methylmorpholine / CH₂Cl₂ / 1 h, 0 deg C, then 30 min, room t.

2: N-methylmorpholine / diethyl ether / 40 min, 0 deg C, then 50 min, room t.

3: diethyl ether / 0 deg C, then 16 h, room t.

4: 82 percent / Rh(OAc)2 / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 7 percent / H₂ / Rh/act. Al₂O₃ / ethanol / 5 h / 50 °C / 3102.9 Torr

6: 1.) THF, 24 h, room t., 2.) THF

7: 48percent aq. HBr / 1 h / 80 °C

With 4-methyl-morpholine; hydrogen bromide; hydrogen; rhodium(II) acetate; Rh/Al₂O₃; In diethyl ether; ethanol; dichloromethane;

DOI:10.1002/hlca.19860690828

Reference yield:

2-(4'-acetoxyphenyl)-3-(pyrrol-1-yl)propionic acid (111751-82-7) → 4-[7-methyl-1,2,3,5,8,8a-hexahydroindolizin-6-yl]phenol (26294-41-7,23506-90-3,31470-47-0)

Guidance literature:

Multi-step reaction with 6 steps

1: N-methylmorpholine / diethyl ether / 40 min, 0 deg C, then 50 min, room t.

2: diethyl ether / 0 deg C, then 16 h, room t.

3: 82 percent / Rh(OAc)2 / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 7 percent / H₂ / Rh/act. Al₂O₃ / ethanol / 5 h / 50 °C / 3102.9 Torr

5: 1.) THF, 24 h, room t., 2.) THF

6: 48percent aq. HBr / 1 h / 80 °C

With 4-methyl-morpholine; hydrogen bromide; hydrogen; rhodium(II) acetate; Rh/Al₂O₃; In diethyl ether; ethanol; dichloromethane;

DOI:10.1002/hlca.19860690828

upstream raw materials:

6-(4-methoxyphenyl)-7-methyl-1,2,3,5,8,8a-hexahydroindolizine

6-(4'-acetoxyphenyl)-1,2,3,5,6,7,8,8a-octahydro-7-methylindolizin-7-yl acetate

6-(4-methoxyphenyl)-7-methyl-2,3,8,8a-tetrahydroindolizin-5(1H)-one

2-(4-Methoxy-phenyl)-1-[2-((E)-3-phenylsulfanyl-allyl)-pyrrolidin-1-yl]-ethanone

Refernces

• 1、 Chea, JongMyoung,Clive, Derrick L. J.. "Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical". . p. 10294 - 10298. Retrieved 2015/11/03.
• 2、 Danishefsky, Samuel J.,Vogel, Claus. "A Concise Total Synthesis of (+/-)-Ipalbidine by Application of the Aldimine-Diene Cyclocondensation Reaction". . p. 3915 - 3916. Retrieved 2007/10/02.