(S)-allethrolone acetate | 22373-76-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-allethrolone acetate
• 英文别名: (S)-2-methyl-3-(2-propenyl)-4-oxo-2-cyclopenten-1-yl acetate；(1S)-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene；1S-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene；Allethrolon-acetat；(1S)-2-Methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl acetate；[(1S)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] acetate
• CAS: 22373-76-8
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: MDFPPPIHFJPKRF-NSHDSACASA-N

物化性质

• 沸点：
  279.8±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-allethrolone acetate 生成 1S-acetoxy-2-methyl-3-allyl-4-fluorochloromethylene-cyclopent-2-ene
  参考文献：
  名称：

  Novel allethrolone derivatives

  摘要：

  化学式为##STR1##的新型醇类化合物，其中R.sub.1和R.sub.2分别选自羰酰基和R.sub.1 '和R.sub.2 '，R.sub.1 '和R.sub.2 '分别选自氢、卤素、1至6个碳原子的烷基、6至10个碳原子的芳基、7至13个碳原子的芳基烷基、2至5个碳原子的烷氧羰基和--CN，R.sub.3和R.sub.3 '分别选自氢、1至3个碳原子的烷基和2至3个碳原子的烯基，以S形式、R形式或它们的消旋混合物，其与环丙烷羧酸酯具有较高杀虫活性，并提供其制备方法。

  公开号：

  US04304733A1
• 作为产物：
  描述：

  S-烯丙醇酮 在 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-allethrolone acetate
  参考文献：
  名称：

  Novel allethrolone derivatives

  摘要：

  化学式为##STR1##的新型醇类化合物，其中R.sub.1和R.sub.2分别选自羰酰基和R.sub.1 '和R.sub.2 '，R.sub.1 '和R.sub.2 '分别选自氢、卤素、1至6个碳原子的烷基、6至10个碳原子的芳基、7至13个碳原子的芳基烷基、2至5个碳原子的烷氧羰基和--CN，R.sub.3和R.sub.3 '分别选自氢、1至3个碳原子的烷基和2至3个碳原子的烯基，以S形式、R形式或它们的消旋混合物，其与环丙烷羧酸酯具有较高杀虫活性，并提供其制备方法。

  公开号：

  US04304733A1

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。
• 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.
• Process for producing optically active cyclopentenolones
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0127386B1

  公开（公告）日：1987-08-05
• US4304733A
  申请人：——

  公开号：US4304733A

  公开（公告）日：1981-12-08
• US4356187A
  申请人：——

  公开号：US4356187A

  公开（公告）日：1982-10-26