56912-83-5

Basic information

• Product Name: 16-Azabicyclo10.3.1hexadeca-1(16),12,14-triene, 3-methyl-
• Synonyms: 16-Azabicyclo10.3.1hexadeca-1(16),12,14-triene, 3-methyl-
• CAS NO: 56912-83-5
• Molecular Formula: C₁₆H₂₅N
• Molecular Weight: 0
• Mol File: 56912-83-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 16-Azabicyclo10.3.1hexadeca-1(16),12,14-triene, 3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 16-Azabicyclo10.3.1hexadeca-1(16),12,14-triene, 3-methyl-(56912-83-5)
• EPA Substance Registry System: 16-Azabicyclo10.3.1hexadeca-1(16),12,14-triene, 3-methyl-(56912-83-5)

Safety Data

• Hazardous Substances Data: 56912-83-5(Hazardous Substances Data)

Usage

Bicyclic compound

Yes
It has two fused rings in its molecular structure.

Nitrogen atom location

Larger ring
The nitrogen atom is part of the larger ring in the bicyclic structure.

Molecular weight

191.29 g/mol
The mass of one mole of the compound is 191.29 grams.

Physical state

Colorless liquid
The compound appears as a colorless liquid at room temperature.

Molecular structure

Six-membered ring fused to a ten-membered ring with a double bond and a methyl group at the 3-position
The compound has a complex structure with two fused rings, one being six-membered and the other ten-membered, along with a double bond and a methyl group attached to the 3rd carbon atom.

Applications

Organic synthesis, pharmaceutical research, and material science research
The compound is used in various fields of research and has potential applications in the synthesis of other organic compounds, as well as in the development of pharmaceuticals and materials.

Upstream product

• 84099-32-1 2-allyl-12-(phenylselenyl)cyclododecanone 
• 84099-33-2 2-allyl-11-methylcyclododecanone 
• 84099-22-9 (E)-12-Allyl-cyclododec-2-enone 
• 32539-89-2 (+/-)-2-allylcyclododecanone 
• 2402-78-0 2,6-dichloropyridine 
• 84099-24-1 C₁₇H₃₁NO₃S 
• 77128-35-9 7-methylcyclopentadecane-1,5-dione 
• 145095-98-3 14-Methyl-5-nitro-2-<(pentylamino)methyliden>cyclopentadecanon 
• 145095-96-1 2-<3-(1,3-Dioxolan-2-yl)propyl>-11-methyl-2-nitrocyclododecanon 
• 145095-95-0 12-<3-(1,3-Dioxolan-2-yl)propyl>-12-nitrocyclododec-2-enon 
• 145095-94-9 2-<3-(1,3-Dioxolan-2-yl)propyl>-2-nitrocyclododecanon 
• 145095-97-2 4-(4-Methyl-1-nitro-2-oxocyclododecyl)butanal 
• 120269-91-2 4-(1-Nitro-2-oxocyclododec-1-yl)butanal 
• 145096-00-0 3-Methyl-12-nitrocyclopentadecanon 

Downstream Products

• 501-08-6 (+)-muscopyridine 

Relevant articles and documents

Synthesis of (+/-)-Muscopyridine via C-ZIP Ring Enlargement

Treatment of 4-(1-nitro-2-oxocyclododec-1-yl)butanal (1) and of its methyl derivative 5 with pentylamine in EtOH at room temperature gave the ring-enlarged aminomethylidene derivatives 6 and 7, respectively (Scheme 1).After hydrolysis of the aminomethylidene group in 6 and 7 and deformylation followed by a reductive Nef-type reaction, the macrocyclic diketones 10 and 11, respectively, were obtained.They were transformed by a modified Hantzsch procedure to the title compound (+/-)-muscopyridine (13) and normuscopyridine (12), respectively.

A new synthesis of dl-muscopyridine based on the regioselective cyclopentenone annulation

Sulphuric acid catalyzed ring closure of propargyl alcohol dianion adduct of 2-cyclododecenone gives bicyclo[10.3.0]pentadec-1(12),2-dien-13-one. 1,6-Conjugate addition of methyl group followed by ring-expansion and aromatization affords the title compounds.

Regio- and Stereoselective Cyclopentannulation with Ketones and Propargyl Alcohol Derivatives. Synthesis of dl-Nootkatone and dl-Muscopyridine

A highly regio- and stereoselective five-membered ring annulation involving the acid-treatment of propargyl alcohol dianion adducts of ketones is described.The propargyl alcohol adduct of 2-octanone was converted into 2-methyl-3-pentyl-2-cyclopentenone by treatment with sulfuric acid-methanol (1:1) at 0 deg C.As the major product, 1-methylbicyclodec-6-en-8-one was produced from 2-methylcycloheptanone.Remarkable regioselective cyclopentannulation was observed in 2-methylcyclohexanone and 2,3-dimethylcyclohexanone wherein 1-methyl- and trans-1,2-dimethyl-substituted bicyclonon-5-en-7-one (BNO) are produced, respectively.With 3-butyn-2-ol, 2-methylcyclohexanone was converted into the cis-1,9-dimethyl-substituted BNO. 4-Isopropyl-2-methylcyclohexanone was transformed into an 83-85:17-15 mixture of c-3-isopropyl-r-1,c-9-dimethyl-BNO and its 3-epimer.These results are explained in terms of the conrotatory ring-closure of thermodynamically most favorable hydroxypentadienyl cation intermediates. 3-Methoxycarbonyl-cis-1,9-dimethyl-BNO produced from 4-methoxycarbonyl-2-methylcyclohexanone and 3-butyn-2-ol was successfully transformed into dl-nootkatone by converting the methoxycarbonyl group into isopropenyl of correct stereochemistry followed by ring enlargement.Cyclopentannulation using propargyl alcohol dianion adducts of 2-cycloalkenones is discussed.Annulation takes place regioselectively to give conjugated dienones, e.g., (E)-bicyclopentadeca-1(12),2-dien-13-one from 2-cyclododecenone.This product is led to dl-muscopyridine by conjugate 1,6-addition of methyl group followed by ring expansion and finally by aromatization with hydroxylamine hydrochloride.