(1R,3S)-3-[(4R)-2,5-dioxoimidazolidin-4-yl]-1,2,2-trimethylcyclopentanecarboxamide | 1398121-06-6

• 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: (1R,3S)-3-[(4R)-2,5-dioxoimidazolidin-4-yl]-1,2,2-trimethylcyclopentanecarboxamide
• 英文别名: (1R,3S)-3-[(4R)-2,5-dioxoimidazolidin-4-yl]-1,2,2-trimethylcyclopentane-1-carboxamide
• CAS: 1398121-06-6
• 化学式: C₁₂H₁₉N₃O₃
• 分子量: 253.301
• InChiKey: GWTVBTQRFQDQMR-QHMRUWFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3S)-3-[(4R)-2,5-dioxoimidazolidin-4-yl]-1,2,2-trimethylcyclopentanecarboxamide 在 barium hydroxide octahydrate 、 水 作用下， 反应 24.0h， 以82%的产率得到5,8,8-trimethyl-4-oxo-3-azabicyclo[3.2.1]octane-2-carboxylic acid
  参考文献：
  名称：

  Diastereospecific ring cleavage of bornane-2,3-dione in the Bucherer-Bergs reaction

  摘要：

  A novel regio- and diastereospecific ring cleavage of bornane-2,3-dione (camphor quinone) under Bucherer-Bergs reaction conditions has been investigated. The simplicity of this transformation provides a novel and straightforward synthetic pathway to enantiopure derivatives of cyclopentane carboxylic acid as well as functionalized hydantoins in just two steps, starting from inexpensive and easily available camphor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.003
• 作为产物：
  描述：

  potassium cyanide 、 (1R)-(-)-樟脑醌 在 碳酸氢铵 作用下， 以 乙醇 、 水 为溶剂， 反应 48.17h， 以75%的产率得到(1R,3S)-3-[(4R)-2,5-dioxoimidazolidin-4-yl]-1,2,2-trimethylcyclopentanecarboxamide
  参考文献：
  名称：

  Diastereospecific ring cleavage of bornane-2,3-dione in the Bucherer-Bergs reaction

  摘要：

  A novel regio- and diastereospecific ring cleavage of bornane-2,3-dione (camphor quinone) under Bucherer-Bergs reaction conditions has been investigated. The simplicity of this transformation provides a novel and straightforward synthetic pathway to enantiopure derivatives of cyclopentane carboxylic acid as well as functionalized hydantoins in just two steps, starting from inexpensive and easily available camphor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.003