(1S,4R)-2-(2-tert-butylphenyl)-2-azabicyclo[2.2.0]hex-5-en-3-one | 1336437-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (1S,4R)-2-(2-tert-butylphenyl)-2-azabicyclo[2.2.0]hex-5-en-3-one
• CAS: 1336437-80-9
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: RYDDEVDHPULLIH-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-叔丁基苯胺 在 正丁基锂 、 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 、 二异丙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 15.0h， 生成 (1R,4S)-2-(2-tert-butylphenyl)-2-azabicyclo[2.2.0]hex-5-en-3-one 、 (1S,4R)-2-(2-tert-butylphenyl)-2-azabicyclo[2.2.0]hex-5-en-3-one
  参考文献：
  名称：

  Light-Induced Enantiospecific 4π Ring Closure of Axially Chiral 2-Pyridones: Enthalpic and Entropic Effects Promoted by H-Bonding

  摘要：

  Nonbiaryl axially chiral 2-pyridones were synthesized and employed for light-induced electrocyclic 4 pi ring closure leading to bicyclo-beta-lactam photoproducts in solution. The enantioselectivity in the photoproducts varied from 22 to 95% depending on the reaction temperature and the ability of the axially chiral chromophore to form intramolecular and/or intermolecular H-bonds with the solvent. On the basis of the differential activation parameters, entropic control of the enantiospecificity was observed for 2-pyridones lacking the ability to form H-bonds. Conversely, enthalpy played a significant role for 2-pyridones having the ability to form H-bonds.

  DOI：

  10.1021/ja203087a

文献信息

• Light-Induced Enantiospecific 4π Ring Closure of Axially Chiral 2-Pyridones: Enthalpic and Entropic Effects Promoted by H-Bonding
  作者：Elango Kumarasamy、Josepha L. Jesuraj、Joseph N. Omlid、Angel Ugrinov、Jayaraman Sivaguru

  DOI：10.1021/ja203087a

  日期：2011.11.2

  Nonbiaryl axially chiral 2-pyridones were synthesized and employed for light-induced electrocyclic 4 pi ring closure leading to bicyclo-beta-lactam photoproducts in solution. The enantioselectivity in the photoproducts varied from 22 to 95% depending on the reaction temperature and the ability of the axially chiral chromophore to form intramolecular and/or intermolecular H-bonds with the solvent. On the basis of the differential activation parameters, entropic control of the enantiospecificity was observed for 2-pyridones lacking the ability to form H-bonds. Conversely, enthalpy played a significant role for 2-pyridones having the ability to form H-bonds.