3796-64-3Relevant academic research and scientific papers
Synthesis method of teprenone and intermediate thereof
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Paragraph 0080; 0081, (2021/08/19)
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.
Novel intermediate for synthesizing teprenone and application of novel intermediate
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Paragraph 0045; 0066-0069, (2019/04/17)
The invention discloses a novel intermediate for synthesizing teprenone. The novel intermediate is a compound shown as a formula 5. The novel intermediate has the advantages that process routes for synthesizing the teprenone by the compound shown as the formula 5 are simple, raw materials are easily available, reaction conditions are mild, side reaction rarely can be carried out, and accordingly the novel intermediate is favorable for industrial production; the high-purity teprenone can be obtained by the aid of the process routes without rectification, and the requirements on ratios of isomermono-cis-form (5Z, 9E and 13E) to all-trans-forms (5E, 9E and 13E) of the teprenone can be met.
A process for the preparation of Teprenone
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Paragraph 0025-0026, (2016/10/07)
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.
Superacidic low-temperature cyclization of terpenols and their acetates
Vlad, P. F.,Ungur, N. D.,Nguen Van Hung,Perutsky, V. B.
, p. 2391 - 2403 (2007/10/03)
The superacidic low-temperature cyclization of terpenols and their acetates be fluorosulfonic acid represents a highly efficient chemo- and structurally selective and stereospecific process.Homoallylic alcohols (α-isomers of cycloterpenols) are the products of cyclization of terpenols; the configuration of the hydroxymethyl group in the products is predetermined by the configuration of the allylic double bond in aliphatic or partially cyclized precursors.The cyclization of terpenyl acetates yields monoacetates of fully cyclized diastereomeric primary-tertiary γ-diols.Their stereochemistry also depends on the configuration of the allylic double bond in the starting substrates. - Key words: terpenols; terpenyl acetates; cyclization, fluorosulfonic acid, drimanes, isoagathanes, scarlanes.
Structure and Biosynthesis of Cleomeprenols from the Leaves of Cleome spinosa
Suga, Takayuki,Shishibori, Tsuyoshi
, p. 2098 - 2104 (2007/10/02)
Cleomeprenols isolated from Cleome spinosa L. (Capparidaceae) have been identified as nonaprenol (1), decaprenol (2), and undecaprenol (3), which are composed of an ω-terminal isoprene, three internal E-isoprene, and the remaining Z-isoprene residues, respectively.Feeding experiments using stereospecifically double-labelled radioactive mevalonate showed that all the cleomeprenols are composed of four biogenetically E- and the remaining biogenetically Z-isoprene residues.Occurence of the succesive cis-condensation of isoprene residues with (2E,6E,10E)-geranylgeranyl pyrophosphate was demonstrated by comparing the incorporation of a homologue of all-E-prenyl pyrophosphates with that of the corresponding 2Z-isomer.
