CID 13917405

Base Information

• Chemical Name: CID 13917405
• CAS No.: 6545-99-9
• Molecular Formula: C15H14O4
• Molecular Weight: 258.274
• Hs Code.: 2932209090
• Metabolomics Workbench ID: 138512
• Nikkaji Number: J407.340A
• Wikidata: Q105361307
• Mol file: 6545-99-9.mol

Synonyms:phebalosin

Chemical Property of CID 13917405

Chemical Property:

• Vapor Pressure: 3.18E-07mmHg at 25°C
• Melting Point: 120.5-121.5 °C
• Refractive Index: 1.584
• Boiling Point: 418.8 °C at 760 mmHg
• Flash Point: 187.7 °C
• PSA: 51.97000
• Density: 1.255g/cm³
• LogP: 2.81760
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 258.08920892
• Heavy Atom Count: 19
• Complexity: 428

Purity/Quality:

99% ^*data from raw suppliers

Phebalosin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1C(O1)C2=C(C=CC3=C2OC(=O)C=C3)OC
• Isomeric SMILES: CC(=C)[C@H]1[C@@H](O1)C2=C(C=CC3=C2OC(=O)C=C3)OC
• General Description: Phebalosin is an epoxy coumarin compound that serves as a precursor in the acid-catalyzed rearrangement to form murralongin, a coumarin derivative with an unusual isoprenoid unit. Its structure features a 7-methoxy-8-[(2R,3R)-3-(1-methylethenyl)oxiranyl]chromen-2-one framework, which undergoes rearrangement under acidic conditions, leading to ring opening and migration to generate an aldehyde functionality. The revised structure of murralongin was confirmed through spectroscopic and crystallographic analysis, highlighting phebalosin's role in this transformation.

Technology Process of CID 13917405

There total 5 articles about CID 13917405 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: 28.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 8-(3-acetyloxiran-2-yl)-7-methoxy-2H-chromen-2-one (600173-56-6) → 8-(3-isopropenyloxiran-2-yl)-7-methoxy-2H-chromen-2-one (6545-99-9)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; at 0 - 20 ℃; for 20h;

DOI:10.1016/S0040-4020(03)00624-0

Reference yield:

7-hydroxy-8-iodocoumarin (65763-00-0) → 8-(3-isopropenyloxiran-2-yl)-7-methoxy-2H-chromen-2-one (6545-99-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / K₂CO₃ / acetone / 5 h / Heating

2.1: isopropylmagnesium chloride / tetrahydrofuran / -78 °C

2.2: 75 percent / tetrahydrofuran / -78 - 20 °C

3.1: 65 percent / K₂CO₃ / acetonitrile / 30 h / 20 °C

4.1: 28 percent / iPr₂NH; nBuLi / tetrahydrofuran / 20 h / 0 - 20 °C

With n-butyllithium; isopropylmagnesium chloride; potassium carbonate; diisopropylamine; In tetrahydrofuran; acetone; acetonitrile; 3.1: Darzens condensation / 4.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00624-0

Reference yield:

7-methoxy-8-iodo-2H-chromen-2-one (65763-01-1) → 8-(3-isopropenyloxiran-2-yl)-7-methoxy-2H-chromen-2-one (6545-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / -78 °C

1.2: 75 percent / tetrahydrofuran / -78 - 20 °C

2.1: 65 percent / K₂CO₃ / acetonitrile / 30 h / 20 °C

3.1: 28 percent / iPr₂NH; nBuLi / tetrahydrofuran / 20 h / 0 - 20 °C

With n-butyllithium; isopropylmagnesium chloride; potassium carbonate; diisopropylamine; In tetrahydrofuran; acetonitrile; 2.1: Darzens condensation / 3.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00624-0

upstream raw materials:

Methyltriphenylphosphonium bromide

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

7-hydroxy-8-iodocoumarin

7-methoxy-8-iodo-2H-chromen-2-one

Downstream raw materials:

murralongin

7-methoxy-2-oxo-2H-chromene-8-carbaldehyde

Minumicrolin

minumicrolin

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.