3772-54-1

Basic information

• Product Name: (5xi)-12-methoxy-13-methylpodocarpa-8,11,13-trien-7-one
• CAS NO: 3772-54-1
• Molecular Formula: C₁₉H₂₆O₂
• Molecular Weight: 286.4085
• Mol File: 3772-54-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 410.5°C at 760 mmHg
• Flash Point: 168.2°C
• Density: 1.029g/cm³
• Vapor Pressure: 5.97E-07mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: (5xi)-12-methoxy-13-methylpodocarpa-8,11,13-trien-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5xi)-12-methoxy-13-methylpodocarpa-8,11,13-trien-7-one(3772-54-1)
• EPA Substance Registry System: (5xi)-12-methoxy-13-methylpodocarpa-8,11,13-trien-7-one(3772-54-1)

Safety Data

• Hazardous Substances Data: 3772-54-1(Hazardous Substances Data)

Upstream product

• 107543-23-7 (+/-)-12-Methoxy-13-mercaptomethyl-5α-podocarpatrien-7-on 
• 110530-31-9 O-Methyl-7-methyl-podocarpinal-semicarbazon 
• 107782-35-4 (+/-)-12-Methoxy-13-chlormethyl-5α-podocarpatrienon-(7) 
• 32301-81-8 (+/-)-12-Methoxy-5α-podocarpatrienon-(7) 
• 15340-76-8 (4bR,8aR)-4b,8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol 
• 123060-89-9 ((4bR,8aR)-3-Hydroxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-ylmethyl)-trimethyl-ammonium; iodide 
• 140408-06-6 ethyl 3-(4-methoxy-3-methylphenylethyl)-2-methyl-4-oxocyclohex-2-encarboxylate 
• 123060-88-8 (+/-)-12-hydroxy-13-dimethylaminopodocarpa-8,11,13-triene 
• 123083-83-0 2-(4-methoxy-3-methylphenylethyl)-3,3-dimethylcyclohexan-1-one 
• 72444-79-2 (+/-)-deoxynimbiol 
• 123083-81-8 2-(4-methoxy-3-methylphenylethyl)-1,3,3-trimethylcyclohexanol 
• 123083-82-9 2-(4-methoxy-3-methylphenylethyl)-3-methylcyclohex-2-en-1-one 
• 69919-95-5 2-(3-methyl-4-methoxyphenyl)ethyl bromide 
• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 

Downstream Products

• 561-95-5 nimbiol 

Relevant articles and documents

Facile total synthesis of (±)-nimbiol

A facile total synthesis of (±)-nimbiol 1 has been achieved. In order to decrease the dioxo byproduct 2a, an improved oxidation system of CrO3/H2O/HOAc/NaOAc was used.

Facile transformation of 1-methoxynaphthalenes to octahydrophenanthrenes. Application to the total synthesis of (±)-sempervirol methyl ether, (±)-sugiol methyl ether, (±)-nimbiol methyl ether, and (±)-nimbidiol dimethyl ether

An efficient general method has been developed for the synthesis of the tricyclic aromatic ketones 4, 12, 13 and 14 from the 1-methoxynaphthalenes 8, 9, 10 and 11 respectively. The transformations of the ketones 4, 12, 13 and 14 into the diterpene ethers (±)-sempervirol methyl ether (7), (±)-sugiol methyl ether (15), (±)-nimbiol methyl ether (16), and (±)-nimbidiol dimethyl ether (17) have been successfully accomplished involving reductive methylation in liquid ammonia as the key reaction.

INFLUENCE OF METHOXY- AND METHYL-AROMATIC SUBSTITUENS ON STEREOCHEMISTRY OF THE PRODUCTS IN THE ACID-CATALIZED CYCLIZATION OF 2-(2-ARYLETHYL)-1,3,3-TRIMETHYLCYCLOHEXANOLS: STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)- NIMBIDIOL AND (+/-)-NIMBIOL

The distributions of the trans- and the cis-podocarpatrienes (5c-g) and (6c-g) in the cyclialkylation reaction of the easily accesible cyclohexanols (4c-g) under a mild condition have been investigated.The cyclohexanol precursors having unactivated aromatic ring proceeds with high stereoselectivity leading to the respective trans-products, while the substrates with an electron donating methoxy or a methyl substituent with respect to the site of electrophilic attack result in the corresponding cis- and the trans-product mixtures.Consistent mechanisms for these stereochemical results have been advanced.Based on these results simple synthesis of the modified diterpenes (+/-)-nimbidiol (7) and (+/-)-nimbiolmethylether (18) have been realized.