(R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one | 54225-47-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one
• 英文别名: (R)-allethrolone；(4R)-2-allyl-4-hydroxy-3-methyl-cyclopent-2-enone；(4R)-2-Allyl-4-hydroxy-3-methyl-cyclopent-2-enon；1(R)-hydroxy-2-methyl-3-(2-propen-1-yl)-cyclopent-2-en-4-one；(R)-4-hydroxy-3-methyl-2-(2-propenyl)cyclopent-2-en-1-one；(R)-Allethrolon；(4R)-4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one
• CAS: 54225-47-7
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: KZYVOZABVXLALY-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one 、 甲基磺酰氯 生成 (R)-2-methyl-3-(2-propenyl)-4-oxo-2-cyclopenten-1-yl methanesulfonate
  参考文献：
  名称：

  MARTEL, J.;TESSIER, J.;DEMOUTE, J. -P.

  摘要：

  DOI：
• 作为产物：
  描述：

  (4R)-2-allyl-4-hydroxy-3-methyl-cyclopent-2-enone semicarbazone 在 potassium hydrogensulfate 、 乙醚 作用下， 生成 (R)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  ALLETHRIN. RESOLUTION OF dl-ALLETHROLONE AND SYNTHESIS OF THE FOUR OPTICAL ISOMERS OF trans-ALLETHRIN

  摘要：

  DOI：

  10.1021/jo01368a027

文献信息

• Preparation of optically active secondary alcohols by combination of enzymatic hydrolysis and chemical transformation
  作者：Hidenori Danda、Toshio Nagatomi、Akira Maehara、Takeaki Umemura

  DOI：10.1016/s0040-4020(01)96192-7

  日期：1991.10

  Several kinds of optically active secondary alcohols (S)-2, which are important intermediates of bioactive compounds, were prepared from the corresponding racemic acetate (±)-1 in high chemical and optical yields by combination of enzymatic hydrolysis and chemical transformation.

  几种旋光仲醇（S）-2是生物活性化合物的重要中间体，它们是通过酶水解和化学转化相结合，由相应的外消旋乙酸酯（±）-1以高化学和光学收率制备的。
• Production of optically active cyclopentenolones
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04552703A1

  公开（公告）日：1985-11-12

  Optically active cyclopentenolones, useful as an intermediate to be directed to pyrethroid insecticide, are produced starting from the optically active cyclopentenolones with the opposite configuration, through the formation of their nitrate ester, followed by the hydrolysis with inversion of configuration.

  具有光学活性的环戊烯酮酮，可用作中间体，用于制备拟除虫菊酯类杀虫剂。从具有相反构型的光学活性环戊烯酮酮开始，通过形成它们的硝酸酯，随后通过反向构型的水解反应产生。
• Nouveaux éthers dont les restes organiques comportent des atomes chiraux, leur procédé de préparation et leur application au dédoublement des alcools, des phénols ou de certains composés de structure lactonique
  申请人：ROUSSEL-UCLAF

  公开号：EP0004493A1

  公开（公告）日：1979-10-03

  Nouveaux éthers dont les restes organiques comportent des atomes chiraux, leur procédé de préparation et leur application au dédoublement des alcools, des phénols ou de certains composés de structure lactonique. L'invention concerne les nouveaux composés de formule 1: dans laquelle A est une chaîne hydrocarbonée de 1 à 10 chaînons, pouvant comporter un ou plusieurs hétéroatomes, une ou plusieurs insaturations et pouvant être de type mono ou polycyclique, y compris spiro ou endo, comportant un ou plusieurs atomes chiraux ou de configuration spatiale entraînant une chiralité, Z est un reste d'alcool ou de phénol comportant au moins un carbone asymétrique, ou de configuration spatiale entraînant une chiralité, Z étant toutefois différent de (R) ou (S) α-cyano 3-phénoxy benzyle lorsque A est une chaîne leur procédé de préparation et leur application au dédoublement des alcools, des phénols ou de certaines lactones.

  有机残基含有手性原子的新醚，其制备工艺及其在醇类、酚类或某些内酯结构化合物的分解中的应用。 本发明涉及式 1 的新化合物： 其中 A 是 1 至 10 元烃链，可含有一个或多个杂原子或一个或多个不饱和基，可为单环或多环类型，包括螺环或内环，含有一个或多个手性原子或具有引起手性的空间构型，Z 是醇或酚残基，含有至少一个不对称碳或具有引起手性的空间构型，但当 A 为链时，Z 不包括(R)或(S)α-氰基-3-苯氧基苄基。 它们的制备方法及其在拆分醇、酚或某些内酯中的应用。
• Esterase gene and its use
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0845534A2

  公开（公告）日：1998-06-03

  Described is a gene coding for an esterase capable of causing asymmetric hydrolysis of an organic carboxylic acid ester of a cyclopentenolone of formula I: wherein R1 is hydrogen or methyl, and R2 is C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C4 haloalkyl, a C5-C9 aliphatic hydrocarbon moiety which may be optionally protected on the terminal hydroxyl group thereof, or a C5-C9 fatty acid residue which may be optionally protected on the terminal carboxyl group thereof, to produce the cyclopentenolone of formula I in (R)-form, an esterase encoded by said gene as well as methods for its production and its use for the industrially favorable production of optically active cyclopentenolones of formula I which serve as the intermediates of drugs, agricultural chemicals, insecticides or other active products.

  所描述的是一种酯酶的编码基因，这种酯酶能使式 I 的环戊烯酮的有机羧酸酯发生不对称水解： 其中 R1 是氢或甲基，R2 是 C1-C10 烷基、C2-C10 烯基、C2-C10 炔基、C1-C4 卤代烷基、C5-C9 脂肪族烃基（其末端羟基可选择受保护）或 C5-C9 脂肪酸残基（其末端羧基可选择受保护）、生产(R)形式的式 I 环戊烯酮的上述基因编码的酯酶及其生产方法，以及将其用于工业化生产具有光学活性的式 I 环戊烯酮（可用作药物、农药、杀虫剂或其他活性产品的中间体）的方法。
• Enzymatic Production of l-Menthol by a High Substrate Concentration Tolerable Esterase from Newly Isolated Bacillus subtilis ECU0554
  作者：Gao-Wei Zheng、Hui-Lei Yu、Jian-Dong Zhang、Jian-He Xu

  DOI：10.1002/adsc.200800412

  日期：2009.2

  Abstractmagnified imageEnzymatic preparation of l‐menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l‐menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E>200) for dl‐menthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dl‐menthyl acetate at 30°C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l‐menthol produced, which were much better than those using commercial enzymes tested. Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l‐menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l‐menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising biocatalyst for the large‐scale enzymatic preparation of l‐menthol. Using this excellent biocatalyst, the enzymatic production of l‐menthol will become a mild, efficient, inexpensive and easy‐to‐use “green chemistry” methodology.