135566-92-6

Basic information

• Product Name: monoterpenylmagnolol
• Synonyms: monoterpenylmagnolol
• CAS NO: 135566-92-6
• Molecular Formula: C₂₈H₃₄O₂
• Molecular Weight: 402.57
• Mol File: 135566-92-6.mol

Chemical Properties

• Boiling Point: 485.6°Cat760mmHg
• Flash Point: 201.2°C
• Appearance: /
• Density: 1.045g/cm³
• Vapor Pressure: 4.68E-10mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: monoterpenylmagnolol(CAS DataBase Reference)
• NIST Chemistry Reference: monoterpenylmagnolol(135566-92-6)
• EPA Substance Registry System: monoterpenylmagnolol(135566-92-6)

Safety Data

• Hazardous Substances Data: 135566-92-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H34O2/c1-6-8-20-11-13-27(29)24(15-20)26-17-21(9-7-2)16-25(28(26)30)23-14-19(5)10-12-22(23)18(3)4/h6-7,11,13-18,22-23,29-30H,1-2,8-10,12H2,3-5H3/t22-,23+/m1/s1

Upstream product

• 1806-29-7 2,2'-dihydroxybiphenyl 
• 57213-53-3 (S)-2-isopropyl-5-carbonylhexanal 
• 100295-52-1 (S)-(-)-4-isopropylcyclohex-2-enone 

Downstream Products

• 138591-17-0 3-((2R,3S)-3-Isopropyl-6-methyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-5,5'-dipropyl-biphenyl-2,2'-diol 
• 138591-16-9 3-((1S,6S)-6-Isopropyl-3-methyl-cyclohex-2-enyl)-5,5'-dipropyl-biphenyl-2,2'-diol 

Relevant articles and documents

Synthesis of (-)-Piperitylmagnolol Featuring ortho-Selective Deiodination and Pd-Catalyzed Allylation

A 1,4-addition strategy using an enone and a copper reagent was studied for the synthesis of (-)-piperitylmagnolol. A MOM-protected biphenol copper reagent was added to BF3·OEt2-activated 4-isopropylcyclohexenone, whereas 1,4-addition of protected monophenol reagents possessing an allyl group was found to be unsuccessful. The allyl group was later attached to the p-,p′-diiodo-biphenol ring by Pd-catalyzed coupling with allylborate. The aforementioned iodide was synthesized using a new method for ortho-selective deiodination of o-,p-diiodophenols.

Synthesis of (-)-Monoterpenylmagnolol and Magnolol

(-)-Monoterpenylmagnolol (3) was synthesized in eight steps from (+)-3,9-dibromocamphor (4) and the bis(methoxymethyl) ether (22) of 3-(4-hydroxyphenyl)-1-propanol.Fragmentation of an endo-3-aryl-9-bromocamphor (27) provided the correct absolute stereochemistry.In this total synthesis, dissolving metal conditions were developed to reduce enol phosphate and isopropenyl functions without concomitant reduction of an attached phenol.Palladium(0)-catalyzed cross-coupling of an arylzinc chloride with 4-allyl-2-iodophenyl methoxymethyl ether (34) provided the desired tricyclic 1,2,3,5-tetrasubstituted biaryl 41 in fair yield without optimization and with little isomerization of the allyl group.Magnolol (1) was also synthesized by aryl coupling of 34 and the methoxymethyl ether of 4-allyl-2-lithiophenol via the zinc chloride method as above, as well as from 5,5'-dibromo-2,2'-dimethoxybiphenyl (37) by allylation with allyltributylstannane followed by ether cleavage.