24851-98-7Relevant academic research and scientific papers
Preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate
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Paragraph 0063; 0067-0069; 0073-0075; 0079-0081; 0085-0087;, (2020/09/20)
The invention relates to a preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. The preparation method of the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate comprises the following step: in the presence of a transition metal complex and a catalytic additive, reacting 2-pentyl-2-cyclopentenone with dimethyl malonate in a reaction solvent to obtain the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. According to the preparation method provided by the invention, a sodium methoxide strong base catalyst is not needed, the generation of salt-containing wastewater is avoided, the method is environment-friendly and high in yield, and meanwhile, the recycling of the catalyst is realized.
Preparation method of methyl dihydrojasmonate
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, (2018/05/01)
The invention discloses an efficient synthesis method of methyl dihydrojasmonate. Under catalysis of homogeneous rhodium and organic nitric oxide, 1-heptyne and ethylene have Pauson-Khand reaction, 2-amyl-2-cyclopentenone is rapidly and efficiently obtained, and an intermediate is subjected to addition and decarboxylation by dimethyl malonate to obtain the methyl dihydrojasmonate. The efficient synthesis method mainly has the advantages that 1-heptyne and ethylene Pauson-Khand reaction yield is effectively improved by the aid of the organic nitric oxide, and usage of rhodium catalysts is reduced. Compared with a traditional methyl dihydrojasmonate production method, the method has the advantages that route steps are short, atom economy is high, the cost is low, and the method is suitable for scale production of the methyl dihydrojasmonate.
Method of manufacturing methylcyclopentanone deriv. (by machine translation)
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, (2018/11/22)
PROBLEM TO BE SOLVED: To provide an efficient method for producing a cyclopentanone derivative usable as an intermediate for a methyl (3-oxocyclopentyl)acetate derivative useful as a perfumery material.SOLUTION: The method for producing the cyclopentanone derivative expressed by general formula (III) comprises Michael addition reaction of a 2-cyclopenten-1-one derivative and an ester compound in the presence of a solid base catalyst containing a phosphazene base or a guanidine base. In the formula, Ris a 1-10C hydrocarbon group; Ris 1-4C alkyl; and Ris 1-4C alkyl or alkoxyl.
Further explorations into the synthesis of Dehydro-Hedione
Winter, Béat,Chapuis, Christian,Brauchli, Robert,De Saint Laumer, Jean-Yves
, p. 246 - 258 (2013/03/28)
Dehydrohedione (DHH) 1 may be obtained in 20% overall yield by a Reformatsky reaction with enone methyl ether 3b, followed by acidic workup of the crude reaction mixture. Alternatively, epoxidation (3-chloroperbenzoic acid, CH2Cl2, 84% yield) of the tertiary allyl alcohol derivative 4 affords a 1: 2 mixture of 8a and 8b. The latter epoxy ester 8b may also be obtained stereoselectively either from 4 (tBuO2H, [Mo(CO)6], 1,2-dichloroethane, 70°, 62% yield; or tBuO2H, [VO(acac)2], decane, 20°, 92% yield), or from 5 (AcOMe, LiN(SiMe3)2, THF, -78°, 84-87%). BF3×Et2O-Catalyzed cascade rearrangement and OH elimination of 8a afford selectively DHH 1 in 88% yield. The cis disposition of the side chains of the weakly odoriferous hedione-like analogues 2b and 2c was maintained by means of either an epoxy or a cyclopropane moiety. Copyright
METHOD FOR PRODUCING OF 2-ALKYL-2-CYCLOALKEN-1-ONE
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Page/Page column 9; 10, (2011/02/26)
The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.
METHOD FOR PRODUCING OF 2-ALKYL-2-CYCLOALKEN-1-ONE
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Page/Page column 14-15, (2011/01/12)
The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.
New jasmonate analogues as potential anti-inflammatory agents
Dang, Hung The,Lee, Hye Ja,Yoo, Eun Sook,Hong, Jongki,Bao, Baoquan,Choi, Jae Sue,Jung, Jee H.
experimental part, p. 10228 - 10235 (2009/04/10)
In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-α) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone (1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA1, PGA2, and 15-deoxy-Δ12,14-PGJ2). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that α-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads.
Highly selective hydrogenation of carbon-carbon multiple bonds catalyzed by the cation [(C6Me6)2Ru2(PPh 2)H2]+: Molecular structure of [(C 6Me6)2Ru2(PPh2)(CHCHPh)H] +, a possible intermediate in the case of phenylacetylene hydrogenation
Tschan, Mathieu J.-L.,Suess-Fink, Georg,Cherioux, Frederic,Therrien, Bruno
, p. 292 - 299 (2007/10/03)
The dinuclear cation [(C6Me6)2Ru 2(PPh2)H2]+ (1) has been studied as the catalyst for the hydrogenation of carbon-carbon double and triple bonds. In particular, [1][BF4] turned out to be a highly selective hydrogenation catalyst for olefin functions in molecules also containing reducible carbonyl functions, such as acrolein, carvone, and methyljasmonate. The hypothesis of molecular catalysis by dinuclear ruthenium complexes is supported by catalyst-poisoning experiments, the absence of an induction period in the kinetics of cyclohexene hydrogenation, and the isolation and single-crystal X-ray structure analysis of the tetrafluoroborate salt of the cation [(C6Me6)2Ru2(PPh 2)-(CHCHPh)H]+ (2), which can be considered as an intermediate in the case of phenylacetylene hydrogenation. On the basis of these findings, a catalytic cycle is proposed which implies that substrate hydrogenation takes place at the intact diruthenium backbone, with the two ruthenium atoms acting cooperatively in the hydrogen-transfer process.
Cycloalkanone composition
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Page/Page column 9, (2008/06/13)
The present invention relates to a cycloalkanone composition which contains cycloalkanone (1) in an amount of 70 wt% or more based on the composition, wherein the content of a dimer of a cycloalkanone represented by formula (2) is 0.055 or less in terms of weight ratio to the cycloalkanone (1), a process for producing the same, a process for producing a composition containing alkyl acetate (5) by using the cycloalkanone composition, and an alkyl acetate composition obtained by the process wherein n is an integer of 1 or 2, R1 and R2 each represent H, a C1 to C8 alkyl group etc., and R3 represents a C1 to C3 alkyl group.
Method of producing acetate derivative
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Page 9, (2008/06/13)
The present invention relates to a method of producing an acetate derivative represented by the formula (II) by demonocarboxylating dimalonate represented by the formula (I), wherein water is supplied while the concentration of water in a demonocarboxylating reaction solution is controlled to 0.4% by weight or less to run demonocarboxylation: wherein n denotes an integer of 1 or 2, R1 and R2 represent H, a C1-8 alkyl group or the like and R3 represents a C1-3 alkyl group.
