8-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

Base Information

• Chemical Name: 8-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one
• CAS No.: 15870-92-5
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.29
• Mol file: 15870-92-5.mol

Synonyms:2H-1-Benzopyran-2-one,8-(1,1-dimethyl-2-propenyl)-7-hydroxy-6-methoxy- (9CI); Coumarin,8-(1,1-dimethylallyl)-7-hydroxy-6-methoxy- (8CI); Obliquetin

Chemical Property of 8-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

Chemical Property:

• PSA: 59.67000
• LogP: 2.97080

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 8-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

There total 3 articles about 8-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one 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%

7-acetoxy-6-methoxy-8-(1,1-dimethylallyl)coumarin (88557-23-7) → 8-(1,1-Dimethylallyl)-scopoletin (15870-92-5)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0040-4020(01)91560-1

Reference yield:

7-(3-methyl-2-butenyloxy)-6-methoxycoumarin (13544-37-1) → 8-(1,1-Dimethylallyl)-scopoletin (15870-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetete / 24 h / Heating

2: 94 percent / 2percent NaOH / methanol

With sodium hydroxide; sodium acetate; In methanol;

DOI:10.1016/S0040-4020(01)91560-1

Reference yield:

→ 8-(1,1-Dimethylallyl)-scopoletin (15870-92-5)

Guidance literature:

Scopoletin 1, Pyrolyse;

DOI:10.1016/S0040-4020(01)92484-6

upstream raw materials:

7-acetoxy-6-methoxy-8-(1,1-dimethylallyl)coumarin

7-(3-methyl-2-butenyloxy)-6-methoxycoumarin

Refernces

10.1016/S0040-4020(01)92484-6

The research aims to elucidate the structures of several natural coumarins found in Ptaeroxylon obliquum (sneezewood) and synthesize them from aesculetin (5). The study confirms the structures of three coumarins (1-3) through UV, NMR, and IR spectroscopy, and demonstrates their interconversion via Claisen rearrangement. The key chemicals involved include aesculetin (5), scopoletin (6), and various derivatives such as 7-mono-ether (8) and 3,3-dimethylallyl bromide. The researchers synthesized coumarin 1 from scopoletin and used pyrolysis to produce obliquetin (2), nieshoutin (3), and an unexpected out-of-ring rearrangement product, 10. Methylation of 10 yielded rutacultin (11). The study concludes that the biogenesis of these coumarins might follow a similar pathway involving Claisen rearrangements, providing valuable insights into the natural synthesis of these compounds and their potential applications.