61262-81-5

Basic information

• Product Name: cannabispiran
• Synonyms: cannabispiran;2',3'-Dihydro-7'-hydroxy-5'-methoxyspiro[cyclohexane-1,1'-[1H]inden]-4-one;Cannabispirone
• CAS NO: 61262-81-5
• Molecular Formula: C15H18O3
• Molecular Weight: 246.3
• Mol File: 61262-81-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 438.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• PKA: 9.76±0.20(Predicted)
• CAS DataBase Reference: cannabispiran(CAS DataBase Reference)
• NIST Chemistry Reference: cannabispiran(61262-81-5)
• EPA Substance Registry System: cannabispiran(61262-81-5)

Safety Data

• Hazardous Substances Data: 61262-81-5(Hazardous Substances Data)

Usage

Uses

Cannabispirone is a natural compound from Cannabis sativa.

Upstream product

• 71135-79-0 cannabispiradienone-A 
• 76898-51-6 (+/-)-cannabispirenone-A 
• 76842-66-5 C₁₆H₂₀O₄ 
• 16909-11-8 3-(3,5-dimethoxyphenyl)acrylic acid 
• 717-94-2 3-(3,5-dimethoxyphenyl)propionic acid 
• 880-87-5 5,7-dimethoxyindan-1-one 
• 64052-90-0 β-cannabispiranol 
• 67-56-1 methanol 
• 83088-39-5 5-methoxy-7-methoxyethoxymethyloxy-1-(3,3-ethylenedioxybutyl)indan-1-carbaldehyde 
• 76842-69-8 5-methoxy-7-methoxyethoxymethyloxyindan-1-spiro-1'-cyclohex-2'-en-4'-one 
• 83088-41-9 5-methoxy-7-methoxyethoxymethyloxy-1-(3-oxobutyl)indan-1-carbaldehyde 
• 76842-62-1 5,7-dimethoxy-1-(3,3-ethylenedioxybutyl)indan-1-carbonitrile 
• 76842-63-2 5,7-dimethoxy-1-(3,3-ethylenedioxybutyl)indan-1-carbaldehyde 
• 76842-72-3 5-methoxy-7-methoxyethoxymethyloxyindan-1-carbonitrile 

Downstream Products

• 69636-83-5 α-cannabispiranol 
• 64052-90-0 β-cannabispiranol 

Relevant articles and documents

Cannabis. XIII. Two new spiro-compounds, cannabispirol and acetyl cannabispirol

Two new spiro-compounds, cannabispirol and acetyl cannabispirol, were isolated along with cannabispirone and cannabispirenone from the Japanese domestic cannabis and these structures were elucidated. The biogenetic relationship of spiro-compounds and cannabinoids was also discussed.

SYNTHESIS OF THE FIVE NATURAL CANNABIS SPIRANS

An efficient route to the O-protected spirenones (2c) and (2d) is described: from these, the five known natural spirans of cannabis, i.e. cannabispiradienone (1a), cannabispirenone-A (2a), cannabispirenone-B (2b), cannabispirone (3a) and cannabispiranol (4a), are synthesised.

Total Synthesis of the Spirans of Cannabis: Cannabispiradienone, Cannabispirenone-A and -B, Cannabispirone, α- and β-Cannabispiranols and the Dihydrophenanthrene Cannithrene-1

O-Methylcannabispirenone has been synthesised (57percent overall from 3,5-dimethoxycinnamic acid) via 5,7-dimethoxyindanone, p-tolylsulphonylmethyl isocyanide conversion into the 1-nitrile, alkylation with 1-iodo-3,3-ethylenedioxybutane, deacetalisation, and spirocyclisation. 5,7-Dimethoxyindanone is 7-deprotected by boron trichloride with high selectivity, and re-protected as the methoxyethoxymethyl ether: following the above route, finally deprotecting by boron trichloride, gives cannabispirenone-A (2) in 21percent overall yield.O-Methylcannabispirenone can be demethylated to give (2) by lithium 1,1-dimethylethanethiolate: demethylation with boron tribromide gives cannabispirenone-B (3).Hydrogenation of synthetic cannabispirenone-A gives cannabispirone (4), reduced by borohydride to the epimeric α-(6) and β-(5) cannabispiranols, separated by h.p.l.c.Dehydrogenation of O-methylcannabispirenone with dichlorodicyanobenzoquinone, followed by lithium 1,1-dimethylethanethiolate demethylation, gives cannabispiradienone (1).Under acidic conditions, the latter undergoes dienone-phenol rearrangement to give cannithrene-1 (8), thus completing the total synthesis of the spiro-cannabinoid group of natural products discussed in the preceding paper.The unsubstituted cannabispirenone parent has also been synthesised.