monoterpenylmagnolol

Base Information

• Chemical Name: monoterpenylmagnolol
• CAS No.: 135566-92-6
• Molecular Formula: C28H34 O2
• Molecular Weight: 402.57
• Mol file: 135566-92-6.mol

Synonyms:[1,1'-Biphenyl]-2,2'-diol,3-[(1S,6S)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]-5,5'-di-2-propenyl-(9CI);[1,1'-Biphenyl]-2,2'-diol,3-[3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]-5,5'-di-2-propenyl-,(1S-trans)-;Piperitylmagnolol;

Chemical Property of monoterpenylmagnolol

Chemical Property:

• Vapor Pressure: 4.68E-10mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 485.6°Cat760mmHg
• Flash Point: 201.2°C
• PSA: 40.46000
• Density: 1.045g/cm³
• LogP: 7.31770

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of monoterpenylmagnolol

There total 13 articles about monoterpenylmagnolol 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: 69.0%

C34H48O2Si → (-)-Monoterpenylmagnolol (135566-92-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/acs.orglett.6b00706

Reference yield:

diethyl ((1S,6S)-6-isopropyl-2',2''-bis(methoxymethoxy)-1,4,5,6-tetrahydro-[1,1':3',1''-terphenyl]-3-yl)phosphate → (-)-Monoterpenylmagnolol (135566-92-6)

Guidance literature:

Multi-step reaction with 8 steps

1: bis(acetylacetonate)nickel(II) / tetrahydrofuran / 3 h / 0 - 20 °C

2: hydrogenchloride / tetrahydrofuran; water / 6 h / 75 - 80 °C

3: N-iodo-succinimide; pyridine / acetonitrile / 2 h / 0 °C

4: pyridine; tetra-(n-butyl)ammonium iodide; boron tribromide / dichloromethane / 3 h / -15 - -10 °C

5: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 1 h / 0 °C

6: triethylamine / dichloromethane / 10 h / 20 °C

7: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; sodium carbonate / water; toluene; ethanol / 2 h / 60 °C

8: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With pyridine; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; bis(acetylacetonate)nickel(II); N-iodo-succinimide; tetrabutyl ammonium fluoride; boron tribromide; tetra-(n-butyl)ammonium iodide; sodium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/acs.orglett.6b00706

Reference yield:

C22H23I3O2 → (-)-Monoterpenylmagnolol (135566-92-6)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane; toluene / 1 h / 0 °C

2: triethylamine / dichloromethane / 10 h / 20 °C

3: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; sodium carbonate / water; toluene; ethanol / 2 h / 60 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; tetrabutyl ammonium fluoride; sodium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1021/acs.orglett.6b00706

upstream raw materials:

(S)-(-)-4-isopropylcyclohex-2-enone

(S)-2-isopropyl-5-carbonylhexanal

2,2'-dihydroxybiphenyl

Downstream raw materials:

3-((2R,3S)-3-Isopropyl-6-methyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-5,5'-dipropyl-biphenyl-2,2'-diol

3-((1S,6S)-6-Isopropyl-3-methyl-cyclohex-2-enyl)-5,5'-dipropyl-biphenyl-2,2'-diol

Refernces

• 1、 Agharahimi, Mohamad R.,LeBel, Norman A.. "Synthesis of (-)-Monoterpenylmagnolol and Magnolol". . p. 1856 - 1863. Retrieved 2007/10/02.