(1R)-1,4,4-trimethyl-2-azabicyclo<3.2.1>octan-3-one | 246044-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (1R)-1,4,4-trimethyl-2-azabicyclo<3.2.1>octan-3-one
• 英文别名: 1,4,4-trimethyl-2-azabicyclo<3.2.1>octan-3-one；(1R,5S)-1,4,4-trimethyl-2-azabicyclo[3.2.1]octan-3-one
• CAS: 246044-18-8
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: JQQOCAUUPQUUEK-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-1,4,4-trimethyl-2-azabicyclo<3.2.1>octan-3-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (1R)-1,4,4-trimethyl-2-azabicyclo<3.2.1>octan-3-thione
  参考文献：
  名称：

  Conformational properties and chiroptical spectra of lactams and thiolactams with 2-azabicyclo[2.2.1]heptane, 2- and 3-azabicyclo[3.2.1]octane skeletons

  摘要：

  The CD spectra of several bicyclic lactams and thiolactams were measured in different solvents. The concentration dependence of the spectra observed in hydrocarbon solvents was attributed to shifts in the equilibrium between monomer and hydrogen-bonded dimer forms. The CD of some compounds is characterized by unusually strong Cotton effects resulting from non-planarity of the amide bonds due to internal strain of the bicyclic skeletons. The X-ray crystallographic structures of 2a,c, 3b,d and 4a,b showed different degrees of distortion of the amide or thioamide moieties from planarity, which causes inherent chirality of the chromophores and profoundly affects the Cotton effect sign and magnitude. This distortion also restricts application of the sector rules for prediction of the n-pi* CD sign, since they can be used only for compounds with planar chromophores. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00262-1
• 作为产物：
  描述：

  (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one oxime 以 甲醇 为溶剂， 反应 15.0h， 以13%的产率得到(1R)-1,4,4-trimethyl-2-azabicyclo<3.2.1>octan-3-one
  参考文献：
  名称：

  氮插入双环[2.2.1]庚酮；（+）-富琴酮和（+）-樟脑1,2的肟的光-贝克曼重排

  摘要：

  在甲醇中，两种天然双环[2.2.1]庚酮（+）-去甲酮和（+）-樟脑肟的肟光解的主要产物是几乎相同数量的两种异构体内酰胺，它们是由光-贝克曼重排和相应的开环酰胺。

  DOI：

  10.1039/c39870001004