(1S)-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene | 38865-66-6

• 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: (1S)-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene
• 英文别名: (RS)-allethrolone acetate；4-acetoxy-2-allyl-3-methyl-2-cyclopentenone；4-acetoxy-2-allyl-3-methyl-cyclopent-2-enone；4-Acetoxy-2-allyl-3-methyl-cyclopent-2-enon；1S-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene；2-Methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl acetate；(2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl) acetate
• CAS: 38865-66-6
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: MDFPPPIHFJPKRF-UHFFFAOYSA-N

物化性质

• 沸点：
  96-97 °C(Press: 0.5 Torr)
• 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：

  (1S)-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene 以 正己烷 为溶剂， 反应 120.0h， 生成 4-Acetoxy-2-cyclopropyl-3-methylcyclopent-2-enon
  参考文献：
  名称：

  2-（丙-2-烯基）环戊-2-烯酮的光化学

  摘要：

  已经研究了几种取代的2-（丙-2-烯基）环戊-2-烯酮的光化学。2-（丙-2-烯基）环戊-2-烯酮（2a; R = OMe或OAc），（6a）和（21）进行二-π-甲烷重排为乙烯基环丙烷[[3a和b），（ 7）和（29）]，而侧链取代的类似物（2b; R = OMe或OAc），（2c; R = OAc）和（6b）在相似条件下进行Z – E异构化。用（2a; R = OAc）进行的敏化和淬灭实验表明（3）源自（2a）的三重激发态。在（2a），（6a）和（21）以及（2b），（2c）和（6b）之间的反应性差异是基于在（分子的侧链。

  DOI：

  10.1039/p19760000249
• 作为产物：
  描述：

  2-丙烯基-3-甲基-4-羟基-2-环戊烯-1-酮 生成 (1S)-acetoxy-2-methyl-3-allyl-4-oxo-cyclopent-2-ene
  参考文献：
  名称：

  2-（丙-2-烯基）环戊-2-烯酮的光化学

  摘要：

  已经研究了几种取代的2-（丙-2-烯基）环戊-2-烯酮的光化学。2-（丙-2-烯基）环戊-2-烯酮（2a; R = OMe或OAc），（6a）和（21）进行二-π-甲烷重排为乙烯基环丙烷[[3a和b），（ 7）和（29）]，而侧链取代的类似物（2b; R = OMe或OAc），（2c; R = OAc）和（6b）在相似条件下进行Z – E异构化。用（2a; R = OAc）进行的敏化和淬灭实验表明（3）源自（2a）的三重激发态。在（2a），（6a）和（21）以及（2b），（2c）和（6b）之间的反应性差异是基于在（分子的侧链。

  DOI：

  10.1039/p19760000249

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。
• Process for preparing 2-cyclopentenone esters
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04535182A1

  公开（公告）日：1985-08-13

  2-Cyclopentenone esters of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is lower alkyl, lower alkenyl, lower alkynyl, or cycloalkyl, cycloalkenyl or substituted or unsubstituted aryl and R.sup.3 is hydrogen or lower alkyl are prepared in high yields by reacting the corresponding racemic or optically active 4-cyclopentenone of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above and R.sup.3 is hydrogen or acyl with at least one lower aliphatic carboxylic acid and/or metal or amine salts thereof.

  公式为：##STR1##其中R.sup.1为氢、低碳基或低烯基，R.sup.2为低碳基、低烯基、低炔基、环烷基、环烯基或取代或未取代芳基，R.sup.3为氢或低碳基。通过将相应的外消旋或光学活性的4-环戊烯酮（公式如下）##STR2##其中R.sup.1和R.sup.2均如上定义，R.sup.3为氢或酰基，与至少一种低脂肪羧酸和/或其金属或胺盐反应，可以高产率地制备出上述公式中的2-环戊烯酮酯。
• 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.
• LaForge et al., Journal of the American Chemical Society, 1952, vol. 74, p. 2392
  作者：LaForge et al.

  DOI：——

  日期：——
• MINAMII, MASAESI;KATSURA, MASASI
  作者：MINAMII, MASAESI、KATSURA, MASASI

  DOI：——

  日期：——