(+/-)-(2-Hydroxymethyl-3,3-dimethylcycloprop-1-yl)acetic acid lactone

• 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: (+/-)-(2-Hydroxymethyl-3,3-dimethylcycloprop-1-yl)acetic acid lactone
• 英文别名: (1S,6R)-7,7-dimethyl-3-oxabicyclo[4.1.0]heptan-4-one
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: GSNQSKKGZHPXNY-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(2-Hydroxymethyl-3,3-dimethylcycloprop-1-yl)acetic acid lactone 在 亚硝酸特丁酯 、 potassium tert-butylate 作用下， 以 甲醇 、 甲苯 为溶剂， 以56%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
• 作为产物：
  描述：

  6,6-dimethylbicyclo[3.1.0]hexan-3-one 在 disodium hydrogenphosphate 、 双氧水 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)-(2-Hydroxymethyl-3,3-dimethylcycloprop-1-yl)acetic acid lactone
  参考文献：
  名称：

  Lochynski, S.; Jarosz, B.; Walkowicz, M., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 2, p. 284 - 288

  摘要：

  DOI：

文献信息

• US7244721B2
  申请人：——

  公开号：US7244721B2

  公开（公告）日：2007-07-17
• 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.
• Lochynski, S.; Jarosz, B.; Walkowicz, M., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 2, p. 284 - 288
  作者：Lochynski, S.、Jarosz, B.、Walkowicz, M.、Piatkowski, K.

  DOI：——

  日期：——