6892-80-4

Basic information

• Product Name: widdrol
• Synonyms: widdrol
• CAS NO: 6892-80-4
• Molecular Formula: C15H26O
• Molecular Weight: 222.36634
• Mol File: 6892-80-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 98 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 303.5°C at 760 mmHg
• Flash Point: 128.4°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 8.86E-05mmHg at 25°C
• Refractive Index: 1.507
• PKA: 14.98±0.60(Predicted)
• CAS DataBase Reference: widdrol(CAS DataBase Reference)
• NIST Chemistry Reference: widdrol(6892-80-4)
• EPA Substance Registry System: widdrol(6892-80-4)

Safety Data

• Hazardous Substances Data: 6892-80-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H26O/c1-13(2)7-5-8-14(3)10-11-15(4,16)9-6-12(13)14/h6,16H,5,7-11H2,1-4H3/t14-,15+/m0/s1

Upstream product

• 75154-37-9 cis-3,4,4a,5,6,7,8,9-octahydro-4a,7-dimethyl-7-vinyl-2H-benzocyclohepten-2-one 
• 107291-63-4 Acetic acid (4aS,7S)-4a-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1,1,7-trimethyl-2,3,4,4a,5,6,7,8-octahydro-1H-benzocyclohepten-7-yl ester 
• 100692-91-9 1-Methoxy-5-methyl-bicyclo[3.2.2]non-6-en-2-one 
• 107291-53-2 (1R,2R,5R)-2-[2-(2-Ethyl-[1,3]dioxolan-2-yl)-ethyl]-1-methoxy-5-methyl-bicyclo[3.2.2]non-6-en-2-ol 
• 107291-53-2 (1R,2S,5R)-2-[2-(2-Ethyl-[1,3]dioxolan-2-yl)-ethyl]-1-methoxy-5-methyl-bicyclo[3.2.2]non-6-en-2-ol 
• 75154-37-9 trans-2,3,4,4a,5,6,7,8,-octahydro-1,1,4a,7-tetramethyl-1H-benzocycloheptene-7-carboxylic acid 
• 116913-98-5 2,6-dimethyl-3-ethoxy-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one 
• 116913-99-6 2,4-dimethyl-4-<2-<(trimethylsilyl)methyl>-2-butenyl>-3-vinyl-2-cyclohexen-1-one 
• 116914-07-9 2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-1H-benzocycloheptene-6-carboxylic acid 
• 116914-00-2 3,4,4a,5,6,7,8,9-octahydro-1,4a,7-trimethyl-6-methylene-2H-benzocyclohepten-2-one 
• 116914-02-4 2,3,4,4a,5,6,7,8-octahydro-6-methylene-1,1,4a,7-tetramethyl-1H-benzocyclohepten-2-one 
• 116914-08-0 2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-1H-benzocycloheptene-6-formaldehyde 
• 116914-06-8 2,3,4,4a,5,6,7,8-octahydro-6-hydroxymethyl-1,1,4a,7-tetramethyl-1H-benzocycloheptene 
• 116914-04-6 2,3,4,4a,5,6,7,8-octahydro-6-methylene-1,1,4a,7-tetramethyl-1H-benzocycloheptene 

Downstream Products

• 94093-53-5 1,1,3-Trimethyl-3-(3,5-dihydroxy-3-methyl-pentyl)-cyclohexanol-⁽²⁾ 

Relevant articles and documents

Intramolecular [4+3] cycloadditions. Towards a synthesis of widdrol

Certain substituted alkoxyallylic sulfones were alkylated and treated with Lewis acids to produce vinylthionium ions that underwent intramolecular [4+3] cycloaddition reactions with a tethered furan. Manipulation of the cycloadduct led to the synthesis of widdrol. Other attempts to prepare the cycloadducts were made, but none were exceptionally better than the route using vinylthionium ions as intermediates. Interesting aspects of the alkylation chemistry of phenylthio-substituted alkoxyallylic sulfones are detailed as well.

REARRANGEMENT APPROACHES TO CYCLIC SKELETONS. V. FORMAL BRIDGEHEAD SUBSTITUTION OF 1-METHOXYBICYCLONON-6-EN-2-ONES AND ITS APPLICATION TO A TOTAL SYNTHESIS OF (+/-)-WIDDROL

The C-1 methoxy group of bicyclonon-6-en-2-ones is replaced by alkyl, alkenyl, and aryl groups or hydrogen with inversion of the absolute configuration via the two-step sequence consists of Grignard reaction or reduction of the carbonyl followed by

Control of Remote Relative Chiralities: A Stereospecific Total Synthesis of dl-Widdrol

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