2-羟甲基-2-氮杂双环[2.2.1]庚-5-烯-3-酮 | 157732-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 2-羟甲基-2-氮杂双环[2.2.1]庚-5-烯-3-酮
• 英文名称: 2-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
• 英文别名: N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one；N-hydroxymethyl vince lactam；2-(Hydroxymethyl)-2-azabicyclo[2.2.1]hept-5-en-3-one
• CAS: 157732-10-0
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: YIVZLGMTDFTBEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-羟甲基-2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮
  参考文献：
  名称：

  Lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones

  摘要：

  The lipase-catalyzed asymmetric resolution of 2-azabicyclo[2.2.1] hept-5-en-3-ones is reported; non-racemic chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification or hydrolysis of N-hydroxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one or N-acyloxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one.

  DOI：

  10.1016/0957-4166(96)00293-5
• 作为产物：
  描述：

  聚合甲醛 、 2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 potassium carbonate 作用下， 反应 6.0h， 以70%的产率得到2-羟甲基-2-氮杂双环[2.2.1]庚-5-烯-3-酮
  参考文献：
  名称：

  Lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones

  摘要：

  The lipase-catalyzed asymmetric resolution of 2-azabicyclo[2.2.1] hept-5-en-3-ones is reported; non-racemic chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification or hydrolysis of N-hydroxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one or N-acyloxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one.

  DOI：

  10.1016/0957-4166(96)00293-5

文献信息

• A facile lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones
  作者：Hiroto Nakano、Yuko Okuyama、Kazuto Iwasa、Hiroshi Hongo

  DOI：10.1016/0957-4166(94)80144-4

  日期：1994.7

  The lipase-catalyzed asymmetric synthesis of optically active 2-azabicyclo[2.2.1]hept-5-en-3-ones is reported. Chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification of 2-hydroxymethyl-2-azabicyclo-[2.2.1]hept-5-en-3-one.
• Enantioselective transesterification of<b><i>N</i></b>-hydroxymethyl vince lactam catalyzed by lipase under ultrasound irradiation
  作者：Fuqiu Li、Dantong Zhao、Ge Chen、Hong Zhang、Hong Yue、Lei Wang、Zhi Wang

  DOI：10.3109/10242422.2013.857314

  日期：2013.12

  Ultrasound has been successfully used to improve the performance of Mucor miehei lipase (MML) in enantioselective transesterifi cation of N-hydroxymethyl vince lactam with vinyl valerate as acyl donor in methyl tert-butyl ether. The effects of reaction conditions have been investigated. Under the optimum conditions (ultrasound power, 175 W; temperature, 30 degrees C; water activity, 0.22; pH, 7.0), the enzyme activity of MML was 93.7 mu mol/g/min and the enantioselectivity (E value) was 68.2. The results also indicated that the free enzyme was stable under low power ultrasound conditions.
• Process for the preparation of optically active azabicyclo heptanone derivatives
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：EP1348765B1

  公开（公告）日：2006-05-24
• Lipase-catalyzed resolution of 2-azabicyclo[2.2.1]hept-5-en-3-ones
  作者：Hiroto Nakano、Kazuto Iwasa、Yuko Okuyama、Hiroshi Hongo

  DOI：10.1016/0957-4166(96)00293-5

  日期：1996.8

  The lipase-catalyzed asymmetric resolution of 2-azabicyclo[2.2.1] hept-5-en-3-ones is reported; non-racemic chiral 2-azabicyclo[2.2.1]hept-5-en-3-ones were obtained conveniently by lipase-catalyzed enantioselective transesterification or hydrolysis of N-hydroxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one or N-acyloxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one.