tert-butyl N-[(1S,5S,6R)-7,7-dimethyl-4-oxo-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate | 1207861-87-7

• 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: tert-butyl N-[(1S,5S,6R)-7,7-dimethyl-4-oxo-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate
• CAS: 1207861-87-7
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: SKOOQHKCBVNLOT-CIUDSAMLSA-N

物化性质

• 沸点：
  396.0±21.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 tert-butyl N-[(1S,5S,6R)-7,7-dimethyl-4-oxo-3-oxabicyclo[4.1.0]heptan-5-yl]carbamate 在 potassium carbonate 作用下， 反应 2.0h， 生成 methyl (2S)-[(tert-butoxycarbonyl)amino][(1R,3S)-3-(hydroxymethyl)-2,2-dimethylcyclopropyl]acetate 、 methyl (2R)-[(tert-butoxycarbonyl)amino][(1R,3S)-3-(hydroxymethyl)-2,2-dimethylcyclopropyl]acetate
  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：

  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

文献信息

• Novel peptides as NS3-serine protease inhibitors of hepatitis C virus
  申请人：Njoroge George F.

  公开号：US20070232549A1

  公开（公告）日：2007-10-04

  The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

  本发明揭示了具有HCV蛋白酶抑制活性的新化合物，以及制备这些化合物的方法。在另一种实施方式中，本发明揭示了包含这些化合物的制药组合物，以及使用它们治疗与HCV蛋白酶相关的疾病的方法。
• US7244721B2
  申请人：——

  公开号：US7244721B2

  公开（公告）日：2007-07-17
• US7592316B2
  申请人：——

  公开号：US7592316B2

  公开（公告）日：2009-09-22
• 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.