8-oxa-9-azabicyclo<3.2.2>non-6-ene | 113340-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: 8-oxa-9-azabicyclo<3.2.2>non-6-ene
• 英文别名: 6-Oxa-7-azabicyclo[3.2.2]non-8-ene
• CAS: 113340-06-0
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: NGCOSXVGHLRGGT-UHFFFAOYSA-N

物化性质

• 沸点：
  169.7±43.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-oxa-9-azabicyclo<3.2.2>non-6-ene 在 palladium on activated charcoal 氯化亚砜 、 氢气 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 氘代氯仿 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 46.5h， 生成 降莨菪鹼
  参考文献：
  名称：

  Synthetic approaches to nortropanes and nortrop-6-enes; intramolecular displacement by nitrogen in 7-membered rings

  摘要：

  The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.

  DOI：

  10.1016/s0040-4020(01)80313-6
• 作为产物：
  描述：

  1,3-环庚二烯 在 tetramethylammonium metaperiodate 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 8-oxa-9-azabicyclo<3.2.2>non-6-ene
  参考文献：
  名称：

  降冰片烷和降冰片烯6烯衍生物的简单方法

  摘要：

  分子内环化的-1-（苄基氨基）-4- chlorocycloheptane和庚-2-烯分别得到相应的8-氮杂双环[3.2.1]辛烷（去甲莨菪烷）和-辛-6-烯（nortrop -6-烯）衍生物。在适当的条件下，环庚-1,3-二烯以75％的总收率转化为降冰片烷。

  DOI：

  10.1016/s0040-4039(01)81095-9

文献信息

• A simple approach to nortropane and nortrop-6-ene derivatives
  作者：Antoinette Bathgate、John R. Malpass

  DOI：10.1016/s0040-4039(01)81095-9

  日期：1987.1

  Intramolecular cyclisation of -1-(benzylamino)-4-chlorocycloheptane and hept-2-ene gives the corresponding 8-azabicyclo[3.2.1]octane (nortropane) and -oct-6-ene (nortrop-6-ene) derivatives respectively. Under appropriate conditions, cyclohepta-1,3-diene is converted into nortropane in 75% overall yield.

  分子内环化的-1-（苄基氨基）-4- chlorocycloheptane和庚-2-烯分别得到相应的8-氮杂双环[3.2.1]辛烷（去甲莨菪烷）和-辛-6-烯（nortrop -6-烯）衍生物。在适当的条件下，环庚-1,3-二烯以75％的总收率转化为降冰片烷。
• Synthetic approaches to nortropanes and nortrop-6-enes; intramolecular displacement by nitrogen in 7-membered rings
  作者：Antoinette Naylor (nee Bathgate)、Nicola Howarth、John R. Malpass

  DOI：10.1016/s0040-4020(01)80313-6

  日期：1993.1

  The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.