(1S,5E,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane-4,5-dione 5-oxime | 1207861-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5E,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane-4,5-dione 5-oxime
• 英文别名: (1S,5E,6R)-5-hydroxyimino-7,7-dimethyl-3-oxabicyclo[4.1.0]heptan-4-one
• CAS: 1207861-81-1
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: DMYFVLRMXZMJRQ-VVTRJGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (1S,5E,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane-4,5-dione 5-oxime 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 生成 tert-butyl N-[(1S,5S,6R)-7,7-dimethyl-4-oxo-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate
  参考文献：
  名称：

  A Facile and Efficient Synthesis of 3,3-Dimethyl Isopropylidene Proline From (+)-3-Carene

  摘要：

  A highly efficient and practical route to 3,4-isopropylidene proline 1, starting from (+)-3-carene, was developed. The three continuous stereocenters were constructed using the inherent chirality of the starting natural product 2. The overall yield for the 12-step synthesis is 34%. The optimized sequence leading to 1 has been successfully applied on a multigram scale, thereby establishing the practicality of this route.

  DOI：

  10.1021/jo9022759
• 作为产物：
  描述：

  (+)-methyl {(1R,3S)-3-[(acetyloxy)methyl]-2,2-dimethylcyclopropyl}acetate 在 亚硝酸特丁酯 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 以36%的产率得到(1S,5E,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptane-4,5-dione 5-oxime
  参考文献：
  名称：

  A Facile and Efficient Synthesis of 3,3-Dimethyl Isopropylidene Proline From (+)-3-Carene

  摘要：

  A highly efficient and practical route to 3,4-isopropylidene proline 1, starting from (+)-3-carene, was developed. The three continuous stereocenters were constructed using the inherent chirality of the starting natural product 2. The overall yield for the 12-step synthesis is 34%. The optimized sequence leading to 1 has been successfully applied on a multigram scale, thereby establishing the practicality of this route.

  DOI：

  10.1021/jo9022759

文献信息

• A Facile and Efficient Synthesis of 3,3-Dimethyl Isopropylidene Proline From (+)-3-Carene
  作者：Latha G. Nair、Anil Saksena、Raymond Lovey、Mousumi Sannigrahi、Jesse Wong、Jianshe Kong、Xiaoyong Fu、Viyyoor Girijavallabhan

  DOI：10.1021/jo9022759

  日期：2010.2.19

  A highly efficient and practical route to 3,4-isopropylidene proline 1, starting from (+)-3-carene, was developed. The three continuous stereocenters were constructed using the inherent chirality of the starting natural product 2. The overall yield for the 12-step synthesis is 34%. The optimized sequence leading to 1 has been successfully applied on a multigram scale, thereby establishing the practicality of this route.