3796-64-3

Basic information

• Product Name: 5,9,13,17-Nonadecatetraen-2-one, 6,10,14,18-tetramethyl-, (5Z,9E,13E)-
• CAS NO: 3796-64-3
• Molecular Formula: C23H38O
• Molecular Weight: 330.554
• Mol File: 3796-64-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 5,9,13,17-Nonadecatetraen-2-one, 6,10,14,18-tetramethyl-, (5Z,9E,13E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5,9,13,17-Nonadecatetraen-2-one, 6,10,14,18-tetramethyl-, (5Z,9E,13E)-(3796-64-3)
• EPA Substance Registry System: 5,9,13,17-Nonadecatetraen-2-one, 6,10,14,18-tetramethyl-, (5Z,9E,13E)-(3796-64-3)

Safety Data

• Hazardous Substances Data: 3796-64-3(Hazardous Substances Data)

Upstream product

• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 1066-26-8 sodium acetylide 
• 1113-21-9 (6E,10E)-geranyllinalool 
• 72324-39-1 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 141-97-9 ethyl acetoacetate 
• 71668-80-9 2E,6E,10E-geranylgeranyl methanesulfonate 
• 51921-98-3 (4E,8E)-ethyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoate 
• 71668-79-6 2(E),8(E)-Farnesyl mesylate 
• 24035-35-6 (2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenoic acid ethyl ester 
• 42207-88-5 (2E,6E,10E)-methyl 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoate 
• 24034-73-9 Geranylgeraniol 
• 24163-93-7 farnesyl bromide 
• 689-67-8 pseudo-ionone 
• 3675-00-1 methyl (E,E)-farnesoate 

Downstream Products

• 22488-05-7 geranylfarnesol 
• 64284-92-0 (E,E,E,E)-geranylfarnesoic acid 

Relevant articles and documents

Synthesis method of teprenone and intermediate thereof

The invention relates to synthesis methods of teprenone and an intermediate thereof. The synthesis of the intermediate all-trans (5E,9E)-farnesyl acetone comprises: 1) in the presence of a catalyst, carrying out a carroll rearrangement reaction on the mixture of 5E-nerolidol and 5Z-nerolidol and hydrocarbonyl acetoacetate to obtain the isomer mixture of (5Z,9Z)-farnesyl acetone, (5Z,9E)-farnesyl acetone, (5E,9Z)-farnesyl acetone, and (5E,9E)-farnesyl acetone, wherein the content of (5E,9E)-farnesyl acetone in the isomer mixture is controlled at more than 18%; and 2) carrying out low-temperature crystallization separation on the isomer mixture in a moderately polar solvent to obtain the all-trans (5E,9E)-farnesyl acetone. According to the present invention, the high-purity all-trans (5E,9E)-farnesyl acetone is obtained by using the mixture of 5E-nerolidol and 5Z-nerolidol as the raw material through the low-temperature crystallization separation, such that the teprenone with the qualified quality can be conveniently obtained.

A process for the preparation of Teprenone

The invention discloses a method for preparing teprenone. The method comprises the following steps: (a) mixing geranyl linalool, acetyl Meldrum's acid and aluminum isopropoxide according to a molar ratio of 1: (1.2-1.5): (0.02-0.1), dissolving the mixture in a paraxylene solvent, heating up to 50-160 DEG C, refluxing for 6-10 hours, cooling and removing the solvent to obtain a teprenone mixture; (b) washing and extracting the teprenone mixture, mixing organic layers, and drying to obtain a crude product of teprenone; (c) carrying out molecular distillation, impurity removal, decompression rectifying and impurity removal on the crude product of teprenone to obtain a teprenone product. The method is simple and easy to control, the conversion rate of the product is high, and the prepared product is high in purity, stable in quality and high in safety, thereby being convenient to promote and use in clinical and industrial production.

STRUCTURALLY SELECTIVE STEREOSPECIFIC CYCLIZATION OF E,E,E,E-GERANYLFARNESOL AND ITS ACETATE BY FLUOROSULFONIC ACID

-