502-69-2Relevant articles and documents
Synthesis of new unsaturated enynes, catalysed by copper (I) complexes
Mignani,Chevalier,Grass,Allmang,Morel
, p. 5161 - 5164 (1990)
The copper (I) catalysed substitution of allylic chlorides by alk-1-ynes leads to the synthesis of new terpene derivatives. An efficient synthesis of phytone is described.
Glycinoprenols: Novel Polyprenols Possessing a Phytyl Residue from the Leaves of Soybean
Suga, Takayuki,Ohta, Shinji,Nakai, Akinori,Munesada, Kiyotaka
, p. 3390 - 3393 (1989)
Three novel polyprenols, named glycinoprenol-9, -10, and -11, in addition to ficaprenols were isolated from the leaves of soybean, Glycine max Merill.The glycinoprenols were found to possess a phytyl residue, four to six internal (Z)-prenyl residues, and a Z α-terminal residue aligned in that order on the basis of their IR, 1H NMR, 13C NMR, and mass spectral data.The configurations of two chiral centers in the phytyl residue were determined to be all R by a combination of chemical and spectroscopic methods.
SYNTHESIS OF NEW UNSATURATED ESTERS, CATALYZED BY PALLADIUM-PHOSPHINE COMPLEXES
Mignani, G.,Grass, F.,Aufrand, M.,Morel, D.
, p. 2383 - 2386 (1989)
The palladium-catalyzed addition of allylic chlorides to carbonucleophiles leads to the formation of new terpene derivatives.A facile and economical route of phytone is described.
Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst
Bennett, Elliot L.,Brookfield, Adam,Guan, Renpeng,Huang, Zhiliang,Mcinnes, Eric J. L.,Robertson, Craig M.,Shanmugam, Muralidharan,Xiao, Jianliang
supporting information, p. 10005 - 10013 (2021/07/19)
The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.
An Efficient Alternative to the Total Synthesis of Isophytol
Yerramreddy, Thirupathi R.,Yiannikouris, Alexandros
, p. 996 - 999 (2022/02/17)
An improved and alternative method for the total synthesis of isophytol from citral via using pseudoionone intermediate was developed and described in this manuscript. This alternative commercially viable approach involves six steps and it represents an alternative method commercially viable over existing published synthetic methods in the literature. This goal was achieved by developing and optimizing an efficient and high yield procedure for the synthesis of a key intermediate i.e. 6,10,14-trimethylpentadectrimethylpentadec-5-en-2-one, by reacting 2-methoxypro-pene with a tertiary alcohol (3,7,11-trimethyldodec-1-ene-3-ol). Isophytol was provided in 58-60% overall yield from citral with >99% purity, evaluated by TLC, GC, and NMR.
Synthesis method and method for synthesizing plant alcohol, isoplant alcohol and geranyl geraniol by using intermediate farnesylacetone (by machine translation)
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, (2020/07/21)
The invention relates to a synthesis method of intermediate farnesyl acetone and a method for synthesizing vitamin E, vitamin K1, vitamin K2 side chain isovegetable alcohol, plant alcohol and geranyl geraniol by using farnesyl acetone, and concretely relates to hydrogenation of 5 - farnesyl -2 - acetone and farnesyl acetone through three Grignard reaction to obtain plant ketone. The farnesyl acetone reacts with the vinyl chloride Grignard reagent to obtain geranyl linalool, the aromatic leaf-based geraniol is rearranged under acid catalysis, or farnesyl acetone is directly reacted with the hydroxyl-protected 2 - chloroethanol Grignard reagent to obtain geraniol. The plant alcohol is reacted with the vinyl chloride Grignard reagent to obtain the plant alcohol, and the plant alcohol is directly reacted with the hydroxyl-protected 2 - chloroethanol Grignard reagent to obtain the plant alcohol. The method has the advantages of cheap and easily available starting materials, short synthetic process steps, low product cost and the like. (by machine translation)
Method for preparing unsaturated ketone
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Paragraph 0042-0050, (2019/04/04)
The invention discloses a method for preparing unsaturated ketone. According to the method, an unsaturated alcohol and 2-alkoxy propylene are adopted as raw materials, an acid resin in a fixed bed aremodified, a Saucy-Marbet reaction is carried out, and unsaturated ketone is synthesized with high selectivity and high yields. According to the method, the modified acid resin is adopted as a catalyst, the problem that a common acid resin is poor in catalysis effect is solved; in addition, a fixed bed reactor is adopted to catalyze reactions, separation of the catalyst from reaction products before and after reactions can be achieved, equipment corrosion and adverse influence of a great amount of acids upon later industrial aftertreatment can be avoided, and the method is an economic and efficient synthesis method.
SYNTHESIS OF ALKYL 2-ACETYL-5,9,13-TRIMETHYLTETRADECA-4,8,12-TRIENOATES AND DERIVATIVES BY A NON-CONTINUOUS PRODUCTION PROCESS
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Page/Page column 13-17, (2019/07/13)
The present invention relates to the manufacturing of a process of alkyl 2- acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and alkyl 2-acetyl-9,13-di- methyl-5-methylenetetradeca-8,12-dienoate as well as 6,10,14-trimethylpenta- deca-5,9,13-trien-2-one and 10,14-dimethyl-6-methylenepentadeca-9,13-dien-2-5 one and 6,10,14-trimethylpentadecan-2-one.
Preparation method for high-purity tocopherol succinate salt
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Paragraph 0050; 0051; 0052; 0053, (2018/09/11)
The invention relates to the field of organic synthesis, specifically to a preparation method for tocopherol succinate salt. The preparation method for the tocopherol succinate salt provided by the invention comprises the following steps: hydrogenating dl-alpha-tocopherol in the presence of a precious metal catalyst, subjecting a hydrogenated product and succinic anhydride to an esterification reaction in the presence of alkali so as to prepare a tocopherol succinate intermediate; and subjecting the tocopherol succinate intermediate to salt-forming. The preparation method for the tocopherol succinate salt provided by the invention can effectively improve the purity of a target product, can effectively reduce the content of a single impurity, and can prepare a calcium salt product with a purity capable of reaching 99.9% or above.
PROCESS FOR THE MANUFACTURE OF 6,10,14-TRIMETHYLPENTADECAN-2-ONE
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Page/Page column 11-12, (2017/07/08)
The present invention is directed to a process for the manufacture of 6,10,14- trimethylpentadecan-2-one ("C18-ketone") comprising the step of hydrogenating a mixture of (5E, 9E)-farnesylacetone and (5Z, 9E)- farnesylacetone with hydrogen in the presence of a catalyst, whereby the catalyst is capable of preferentially hydrogenating carbon-carbon double bonds over carbon-oxygen double bonds. Preferably the catalyst comprises a metal selected from the group consisting of palladium, platinum, rhodium, iridium and nickel and mixtures thereof.
