Panacene

Base Information

• Chemical Name: Panacene
• CAS No.: 66389-39-7
• Molecular Formula: C15H15BrO2
• Molecular Weight: 307.185
• Mol file: 66389-39-7.mol

Synonyms:

Chemical Property of Panacene

Chemical Property:

• Vapor Pressure: 1.6E-05mmHg at 25°C
• Boiling Point: 376.2°C at 760 mmHg
• Flash Point: 161.2°C
• PSA: 18.46000
• Density: 1.426g/cm³
• LogP: 3.90370

Purity/Quality:

PANACENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Panacene

There total 18 articles about Panacene 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: 81.0%

C15H16O2 → (+/-) panacene (66389-39-7,82110-07-4,82838-36-6)

Guidance literature:

With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; In cyclohexane; at 20 ℃; for 5h; diastereoselective reaction;

DOI:10.1021/ol801921d

Reference yield: 81.0%

C15H16O2 → (+/-) panacene (66389-39-7,82110-07-4,82838-36-6)

Guidance literature:

With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; In benzene; diastereoselective reaction;

DOI:10.1016/j.tet.2010.03.096

Reference yield: 75.0%

C15H15BrO2 → (+/-) 1-epibromopanacene (66389-39-7,82110-07-4,82838-36-6)

Guidance literature:

C₁₅H₁₅BrO₂; With mercury(II) diacetate; In benzene; at 20 ℃; for 2h; Inert atmosphere;

With ethane-1,2-dithiol; In benzene; for 0.0166667h;

DOI:10.1021/ol801921d

upstream raw materials:

(2S,3S)-4-Ethyl-2-((Z)-pent-2-en-4-ynyl)-2,3-dihydro-benzofuran-3-ol

4-Ethyl-3-oxo-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester

2-ethyl-6-hydroxybenzoic acid ethyl ester

(2S,3S)-2-Allyl-4-ethyl-2,3-dihydro-benzofuran-3-ol

Refernces

'Aromatic ring umpolung', a rapid access to the main core of several natural products

10.1016/j.tet.2010.03.096

The research explores a novel synthetic strategy for rapidly constructing the core structures of various natural products using the concept of aromatic ring umpolung. The purpose of this study is to develop a versatile and efficient method for synthesizing complex natural product cores by leveraging the reactivity inversion of aromatic rings, specifically through the formation of phenoxenium ions using hypervalent iodine reagents such as (diacetoxyiodo)benzene (DIB). The researchers demonstrate that these highly electrophilic intermediates can react with various nucleophiles, leading to a range of different cores found in natural products through oxidative processes. Key findings include the successful synthesis of tricyclic compounds via a formal [2+3] cycloaddition with furan, the oxidative addition of carbon-based nucleophiles to create quaternary carbon centers, and the development of an oxidative transposition process to generate highly functionalized cores. The study concludes that these methodologies offer rapid access to complex natural product cores, significantly reducing the number of synthetic steps required. This approach not only provides a powerful tool for the synthesis of natural products like panacene, mesembrine, and aspidospermidine but also opens up new strategic opportunities in chemical synthesis by transforming simple phenols into highly functionalized structures.