Murralongin

Base Information

• Chemical Name: Murralongin
• CAS No.: 53011-72-6
• Molecular Formula: C15H14O4
• Molecular Weight: 258.2693
• Hs Code.: 2932209090
• Mol file: 53011-72-6.mol

Synonyms:Murralongin;

Chemical Property of Murralongin

Chemical Property:

• Vapor Pressure: 8.99E-09mmHg at 25°C
• Melting Point: 132-134 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 463.6°Cat760mmHg
• Flash Point: 208.5°C
• PSA: 56.51000
• Density: 1.198g/cm³
• LogP: 2.79390
• Storage Temp.: ?20°C

Purity/Quality:

Analysis control,HPLC≥98% ^*data from raw suppliers

Murralongin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 25-50
• Safety Statements: 45-61

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Murralongin is a naturally occurring coumarin derivative characterized by an unusual isoprenoid unit, formed through the acid-catalyzed rearrangement of the epoxy coumarin phebalosin. Its revised structure (v) was confirmed via NMR spectroscopy and X-ray crystallography, correcting an earlier proposal. The rearrangement mechanism involves ring opening of the epoxide at a carbon atom more capable of stabilizing a positive charge, leading to migration of either a vinyl or coumarin skeleton and the formation of an aldehyde function. This process clarifies the structural and mechanistic basis for murralongin's formation.

Technology Process of Murralongin

There total 13 articles about Murralongin 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: 94.0%

8-(3-isopropenyloxiran-2-yl)-7-methoxy-2H-chromen-2-one → murralongin (53011-72-6)

Guidance literature:

With silica gel; In dichloromethane;

DOI:10.1021/np100146y

Reference yield: 75.0%

isomurralonginol (112606-75-4,147059-16-3) → murralongin (53011-72-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4020(01)80713-4

Reference yield: 55.0%

methanol (67-56-1) + Phebalosin (6545-99-9) → 8-(1,2-dihydroxy-3-methylbut-3-enyl)-7-methoxychromen-2-one (56946-30-6) + 7-methoxy-8-(1'-methoxy-2'-hydroxy-3'-methyl-Δ3'-butenyl)coumarin (109273-96-3,6432-67-3,147731-94-0,147731-95-1,120786-75-6,120786-76-7) + murralongin (53011-72-6)

Guidance literature:

With sulfuric acid; In water; at 60 ℃; for 5h;

DOI:10.1248/cpb.34.3978

upstream raw materials:

methanol

Phebalosin

8-(3-isopropenyloxiran-2-yl)-7-methoxy-2H-chromen-2-one

isomurralonginol

Refernces

Acid-catalyzed rearrangement of an epoxy coumarin phebalosin the revised structure of murralongin

10.1248/cpb.34.3978

The research investigates the acid-catalyzed rearrangement of the epoxy coumarin phebalosin to form murralongin, a naturally occurring coumarin with an unusual isoprenoid unit. The study aims to elucidate the structure of murralongin and understand the rearrangement mechanism. Phebalosin was treated with acid and purified through extraction and chromatography to obtain products. The structure of murralongin was revised from the previously proposed structure (vi) to (v) based on NMR spectroscopy and confirmed by X-ray crystallography. The key chemicals involved include phebalosin as the starting material, sulfuric acid for the rearrangement reaction, and methanol for the formation of an intermediate methanol adduct. The study concludes that the rearrangement involves the migration of either a vinyl or coumarin skeleton to an adjacent carbon, essential for generating an aldehyde function from the epoxide. The revised structure (v) of murralongin was identified, and the mechanism was proposed to involve ring opening of the epoxide at the carbon atom better able to tolerate positive charge.