22460-48-6Relevant articles and documents
Ring-closure reactions. 16. An improved procedure for the synthesis of (2,3)thiophenophan-1-ones and its application to a convenient preparation of dl-muscone
Catoni,Galli,Mandolini
, p. 1906 - 1908 (1980)
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Baker,R. et al.
, p. 802 - 803 (1972)
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Novel synthetic method for muscone
Guo, Yuan,Wu, Xin-Liang,Li, Jian-Li,Xu, Ruo-Qian,Shi, Zhen
, p. 2489 - 2494 (2005)
Muscone is a precious fragrant compound scarce in nature. Many attempts to synthesize this unique natural product have been carried out. In this work, a novel synthetic method for the preparation of muscone from 3-methyl-15- hydroxypentadecanoate is provided. Benzimidazolium salt was used as tetrahydrofolate coenzyme model at formic acid oxidation level and Grignard reagent as nucleophile to which a one-carbon unit was transferred. The biomimetic synthesis of muscone was successfully accomplished using the addition-hydrolysis reaction of benzimidazolium salt with the Grignard reagent. Copyright Taylor & Francis, Inc.
A SIMPLE AND FACILE SYNTHESYS OF d,1-MUSCONE
Taechachoonhakit, Siriwan,Ratananukul, Piniti
, p. 911 - 912 (1986)
An efficient method for the synthesis of d,1-muscone has been developed.
Purification and Characterization of an Enone Reductase from Sporidiobolus salmonicolor TPU 2001 Reacting with Large Monocyclic Enones
Yamamoto, Kazunori,Oku, Yuko,Ina, Atsutoshi,Izumi, Atsushi,Doya, Masaharu,Ebata, Syuji,Asano, Yasuhisa
, p. 3697 - 3704 (2017)
We discovered a novel enone reductase from Sporidiobolus salmonicolor TPU 2001 (SsERD) and expressed the gene in Escherichia coli. The enzyme catalyzed the reduction of (E)-3-methylcyclopentadec-2-en-1-one (E-2), cyclopentadec-2-en-1-one (3), and cyclododec-2-en-1-one (4) to (S)-muscone (S-1), cyclopentadecan-1-one (5), and cyclododecan-1-one (6), respectively. The apparent Km and Vmax values for E-2 were estimated to be 4.9±0.4 μm and 100±1.4 nmol min?1 mg?1, respectively. The enzyme was specific to NADPH, and cysteine residues strongly affected the enzyme activity. The enzyme exhibited the highest activity at pH 8.0 and high stability in the pH range from 4.5 to 11.0. Using 10 mU of the enzyme, S-1 was synthesized from 0.1 mm E-2 with 94.8 % yield and 100 % enantiomeric excess by incubation at pH 7.0 and 30 °C for 60 min. We further successfully constructed an enone reductase with high specific activity by mutation of SsERD. The Y67A variant from SsERD exhibited 4.5 times higher specific activity and 3 times higher catalytic efficiency toward E-2. This is the first report of an enzyme catalyzing the reduction of carbon–carbon double bond of large monocyclic enones.
Regioselectivity and Diastereoselectivity in Free-Radical Macrocyclization
Porter, Ned A.,Lacher, Brigitte,Chang, Vincent H.-T.,Magnin, David R.
, p. 8309 - 8310 (1989)
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Synthesis of macrocyclic ketones by ring-enlargement reactions; A new path to (±)-muscone
Bienz,Hesse
, p. 2146 - 2151 (1987)
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Baker et al.
, p. 515 (1974)
Synthesis of macrocycles by intramolecular ketophosphonate reactions. Stereoselective construction of the 'left-wing' of carbomycin B and a synthesis of dl-muscone from oleic acid
Nicolaou,Seitz,Pavia,Petasis
, p. 4011 - 4013 (1979)
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Nozaki,H. et al.
, p. 1107 - 1112 (1969)
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Method for preparing chiral musk ketone
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Paragraph 0039; 0040; 0043; 0044, (2021/02/09)
A method for preparing chiral muscone is provided. 3-methyl-cyclopentadecane-1,5-dione is adopted as an initial raw material, chiral rhodium and a Br nsted acid are adopted as catalysts, hydrogen is adopted as a reductant, and a chiral muscone product is synthesized in a one-pot manner through asymmetric hydrogenation, hydrogenolysis and other reactions. The method is short and simple in route, high in total yield, low in generation of three types of waste and suitable for industrial production of the chiral muscone.
Method for preparing L-muscone
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Paragraph 0050; 0053, (2020/04/02)
The invention discloses a method for preparing L-muscone. The method comprises the following steps: (1) L-muscone in racemic muscone and a chiral hydroxybenzene compound generate L-enantiomer salt under laser irradiation; and (2) crystallization separation and hydrolysis are performed on the L-enantiomer salt to obtain a L-muscone product, wherein the step (1) is carried out in the presence of a Bronsted acid catalyst. Preferably, after hydrolysis in the step (2), separation, purification and other steps are carried out to obtain the L-muscone product. The raw material used in the method is the racemic muscone with a mature production process; batch production can be realized, diastereomer salifying resolution is carried out by adopting laser irradiation, the product selectivity is greatlyimproved, the method is green, pollution-free, and less in production of three wastes, the chiral hydroxybenzene compound is convenient to recover and reusable, the atom economy is high, the productselectivity is high, and the method is suitable for being used in the fields of biology, medical treatment, medicines, spices, cosmetics and the like.
