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

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:

98% ^*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

Enantiospecific synthesis of an indolizidine alkaloid, (+)-ipalbidine

10.1016/S0040-4039(03)00563-X

The study details the enantiospecific total synthesis of the indolizidine alkaloid (+)-ipalbidine, a nonaddictive analgesic with additional biological activities. The synthesis starts from (?)-pyroglutamic acid and involves several key steps. Initially, the alcohol derived from pyroglutamic acid methyl ester is converted to a tosylate, which is then reacted with a higher-order cuprate reagent to form an olefinic amide. This amide is condensed with a bromide, prepared from an ester through reduction and bromination steps, to yield a diene. The diene undergoes ozonolysis to form a diketone, which is then subjected to an intramolecular McMurry coupling reaction using low-valent titanium to construct the desired carbon-carbon double bond, yielding the core structure of ipalbidine. The final steps include reduction of the amide function and debenzylation to obtain the natural product. The study also explores an alternative synthetic path involving the elimination of a vic-diol function from a major byproduct of the McMurry coupling. The developed synthetic strategy is noted for its potential applicability to the synthesis of other biologically active alkaloids.

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