(1S,5R)-1-甲基-3-氮杂双环[3.1.0]己烷-2,4-二酮 | 148236-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (1S,5R)-1-甲基-3-氮杂双环[3.1.0]己烷-2,4-二酮
• 英文名称: (1S,2R)-1-methyl-1,2-cyclopropanedicarboximide
• 英文别名: (1S,5R)-1-Methyl-3-azabicyclo[3.1.0]hexane-2,4-dione
• CAS: 148236-92-4
• 化学式: C₆H₇NO₂
• 分子量: 125.127
• InChiKey: COOSDAIGFVXLLU-DZSWIPIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5R)-1-甲基-3-氮杂双环[3.1.0]己烷-2,4-二酮 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 1.0h， 以26%的产率得到(1S,5R)-1-methyl-4-thioxo-3-azabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Chiroptical Spectra of 1,2-Cyclopropanedicarboxylic Monothioimides¹

  摘要：

  DOI：

  10.1021/jo961724p
• 作为产物：
  描述：

  (1S,2R)-1-methyl-1,2-cyclopropanedicarboxylic anhydride 在 氨 作用下， 生成 (1S,5R)-1-甲基-3-氮杂双环[3.1.0]己烷-2,4-二酮
  参考文献：
  名称：

  Chiroptical properties of 1,2-cyclopropanedicarboxylic anhydrides and imides. The cyclopropane ring contribution to the Cotton effect

  摘要：

  Several optically active 1,2-cyclopropanedicarboxylic anhydrides and imides were prepared and their chiroptical spectra studied. Despite the strained bicyclic skeleton of these compounds, their CD spectra show an unusual solvent dependence. This phenomenon can be explained in terms of the cyclopropane ring contribution to the Cotton effect. A deviation of the skeleton and the anhydride or imide group from the local C(s) symmetry, shown by MNDO calculations, causes formation of an inherently chiral chromophore constituted by the three-membered ring and neighboring carbonyls. This kind of chromophore is responsible for the observed strong Cotton effects.

  DOI：

  10.1021/jo00064a034

文献信息

• Conformational dependence of the circular dichroism of N-nitrosopyrrolidines
  作者：Tadeusz Polonski、Maria J. Milewska、Andrzej Katrusiak

  DOI：10.1021/ja00077a045

  日期：1993.12

  suhstituted N-nitrosopyrrolidines were prepared and their chiroptical spectra studied. The circular dichroism of monocyclic compounds depends on substituents, solvents, and temperature changes. Some of these N-nitrosamines exhibit bisignate CD curves in the region of n-π * transition. On the contrary, conformationally restrictcd bi- and tricyclic compounds show monosignate Cotton effects, the magnitudes

  制备了几种取代的 N-亚硝基吡咯烷并研究了它们的手性光谱。单环化合物的圆二色性取决于取代基、溶剂和温度变化。这些 N-亚硝胺中的一些在 n-π * 跃迁区域表现出双信号 CD 曲线。相反，构象受限的双环和三环化合物表现出单信号棉花效应，其大小几乎与溶剂无关。双标志 CD 曲线是由处于平衡状态的吡咯烷环的两个半椅构象异构体产生的，并有助于相反的 CD 符号。棉花效应迹象可以通过我们之前制定的“降低对称性”扇区规则来预测
• Chiroptical spectra and molecular geometry of bicyclic dithioimides
  作者：Maria J. Milewska、Maria Gdaniec、Hanna Małuszyńska、Tadeusz Połoński

  DOI：10.1016/s0957-4166(98)00293-6

  日期：1998.9

  Several chiral bicyclic dithioimides were prepared by thionation of the parent imides with Lawesson's reagent. Due to a flexibility of the dithioimide chromophore, their CD spectra show significant solvent dependence. A substantial deviation of the chromophore from planarity was confirmed by the MNDO calculations and crystallographic structures of 4, 5b, 6 and 7. The observed CE sign corresponding to the lowest energy n-pi* transition can be predicted, upon careful examination of the molecular geometry, by the antioctant rule with sector signs opposite to those known for ketones. (C) 1998 Elsevier Science Ltd. All rights reserved.