(1aS,4aS,7aS)-4a-Methyl-tetrahydro-1-oxa-cyclopropa[d]indene-2,5-dione | 223638-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1aS,4aS,7aS)-4a-Methyl-tetrahydro-1-oxa-cyclopropa[d]indene-2,5-dione
• 英文别名: (1S,3S,7S)-7-methyl-2-oxatricyclo[5.3.0.01,3]decane-4,8-dione
• CAS: 223638-01-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: XDEBGJIQJLOPCX-OPRDCNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1aS,4aS,7aS)-4a-Methyl-tetrahydro-1-oxa-cyclopropa[d]indene-2,5-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以20%的产率得到(1aS,4aR,5S,7aS)-5-Hydroxy-4a-methyl-hexahydro-1-oxa-cyclopropa[d]inden-2-one
  参考文献：
  名称：

  Studies towards a total synthesis of the antiprogestine onapristone

  摘要：

  Starting from the readily available Eder-Hajosh ketone 2 a stereoselective method for synthesis of arylated hydrindenone 14 was developed. One pot Li/NH3 reduction and trapping of the generated enolate with activated Michael acceptor gave a properly substituted BCD-ring precursor 22. Attempted B ring closure with the model compound 22 failed under various conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00934-4
• 作为产物：
  描述：

  7A-甲基-2,3,5,6,7,7A-六氢-1H-茚-1,5-二酮 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 以95%的产率得到(1aS,4aS,7aS)-4a-Methyl-tetrahydro-1-oxa-cyclopropa[d]indene-2,5-dione
  参考文献：
  名称：

  Studies towards a total synthesis of the antiprogestine onapristone

  摘要：

  Starting from the readily available Eder-Hajosh ketone 2 a stereoselective method for synthesis of arylated hydrindenone 14 was developed. One pot Li/NH3 reduction and trapping of the generated enolate with activated Michael acceptor gave a properly substituted BCD-ring precursor 22. Attempted B ring closure with the model compound 22 failed under various conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00934-4

文献信息

• Enzymatic Baeyer-Villiger Oxidation of Bicyclic Diketones
  作者：Gianluca Ottolina、Gonzalo de Gonzalo、Giacomo Carrea、Bruno Danieli

  DOI：10.1002/adsc.200505027

  日期：2005.6

  Acinetobacter calcoaceticus was employed for the Baeyer–Villiger oxidation of racemic bicyclic diketones such as the Wieland–Miescher and the Hajos–Parrish diketones and of some of their derivatives. The corresponding lactones were produced in a highly regio- and enantioselective manner. The reactions were carried out using a crude enzyme preparation in aqueous buffer, at room temperature, and the recycling

  来自钙乙酸不动杆菌的环己酮单加氧酶用于外消旋双环二酮（如Wieland-Miescher和Hajos-Parrish二酮）的Baeyer-Villiger氧化及其一些衍生物。相应的内酯以高度区域和对映体选择性的方式产生。在室温下，使用粗酶制剂在水性缓冲液中进行反应，然后使用第二个辅助酶系统进行昂贵的辅酶NADPH的回收。酶促过程简单且易于操作，因此为获得对映纯内酯提供了非常实用的工具。
• CAI, ZU-YUN;WANG, YING, XUASYUEH SYUEHBAO , 46,(1988) N2, S. 1191-1194
  作者：CAI, ZU-YUN、WANG, YING

  DOI：——

  日期：——