3582-26-1

Basic information

• Product Name: (1R)-7β-Ethenyl-1,2,3,4,4a,5,6,7,8,9,10,10aα-dodecahydro-1,4aβ,7-trimethyl-1α-phenanthrenecarboxylic acid methyl ester
• Synonyms: (1R)-7β-Ethenyl-1,2,3,4,4a,5,6,7,8,9,10,10aα-dodecahydro-1,4aβ,7-trimethyl-1α-phenanthrenecarboxylic acid methyl ester
• CAS NO: 3582-26-1
• Molecular Formula: C21H32O2
• Molecular Weight: 316.47758
• Mol File: 3582-26-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 384.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.01±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (1R)-7β-Ethenyl-1,2,3,4,4a,5,6,7,8,9,10,10aα-dodecahydro-1,4aβ,7-trimethyl-1α-phenanthrenecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-7β-Ethenyl-1,2,3,4,4a,5,6,7,8,9,10,10aα-dodecahydro-1,4aβ,7-trimethyl-1α-phenanthrenecarboxylic acid methyl ester(3582-26-1)
• EPA Substance Registry System: (1R)-7β-Ethenyl-1,2,3,4,4a,5,6,7,8,9,10,10aα-dodecahydro-1,4aβ,7-trimethyl-1α-phenanthrenecarboxylic acid methyl ester(3582-26-1)

Safety Data

• Hazardous Substances Data: 3582-26-1(Hazardous Substances Data)

Upstream product

• 1686-62-0 isopimaric acid methyl ester 
• 3730-56-1 pimara-8⁽¹⁴⁾,15-dien-18-oic acid methyl ester 
• 127-27-5 pimaric acid 

Relevant articles and documents

Partial Synthesis of 9,10-Syn Diterpenes via Tosylhydrazone Reduction: (-)-(9β)-Pimara-7,15-diene and (-)-(9β)-Isopimaradiene

(9β)-Pimara-7,15-diene (3), a proposed intermediate in the biosynthesis of the momilactone phytoalexins (1 and 2) from rice, and its C-13 epimer, (9β)-isopimara-7,15-diene (4), were synthesized from methyl pimara- and isopimara-8,15-dien-18-oates (8b and 8a, respectively).Allylic oxidation of 8a and 8b as well as the derived diterpene hydrocarbons 15a and 15b with chromium trioxide-dipyridine complex afforded 8,15-dien-7-ones 9a, 9b, 16a, and 16b (35-54percent).Lithium-ammonia reduction of 9a, 16a, and 16b gave predominantly trans,anti,trans-isopimara- and -pimara-15-en-7-ones 10, 17a, and 17b.In contrast, catecholborane reduction of the tosylhydrazones of 9a and 9b provided methyl (9β)-isopimara- and (9β)-pimara-7,15-dien-20-oates (23a and 23b) having the 9,10-syn stereochemistry.The parent diterpenes, 3 and 4, were obtained by carboxyl-to-methyl conversions.In a collaborative investigation 3 was tentatively identified as one of five diterpene hydrocarbons produced upon incubation of (E,E,E)-geranylgeranyl pyrophosphate with a crude enzyme extract from UV-treated rice plants.

CYCLIZATION OF TRICYCLIC DITERPENOIDS INTO TETRACYCLIC DITERPENOIDS BY THE ACTION OF SUPERACIDS

The cyclization of pimaradienes - the methyl esters of isopimaric (I), pimaric (II), and Δ8,9-isopimaric (III) acids - into tetracyclic diterpenes was realized for the first time by the action of superacids (HSO3F-SO2FCl, SbF5-HSO3F-SO2FCl at -120 deg C), followed by "quenching" of the acid solutions with methanol.