1-Chloro-7-norbornanone | 143936-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Chloro-7-norbornanone
• 英文别名: 1-Chlor-bicyclo<2.2.1>heptanon-(7)；1-Chlorobicyclo[2.2.1]heptan-7-one
• CAS: 143936-05-4
• 化学式: C₇H₉ClO
• 分子量: 144.601
• InChiKey: CBJQDAMRPMRIGG-UHFFFAOYSA-N

物化性质

• 沸点：
  228.3±13.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Chloro-7-norbornanone 在 lithium aluminium tetrahydride 作用下， 生成 1-Chloro-7-norbornanol
  参考文献：
  名称：

  Effects of Bridgehead Substitution on Structure and Reactivity of the 7-Norbornyl Cation

  摘要：

  A systematic investigation was undertaken of the effect of bridgehead substitution on the solvolytic reactivity of 7-norbornyl triflates in aqueous TFE. Methyl substitution increases the rate 60-fold and the effect of multiple substitution is additive. Chlorine, on the other hand, exhibits a combined inductive and resonance effect and decreases the reactivity 1700 times. The observed normal secondary P-deuterium isotope effect of the 1,4-d(2) derivative can be rationalized by assuming a tilted C-s geometry for the cationic transition structure which is only slightly higher in energy than the nonclassical intermediate cation of C-1 symmetry. Bridgehead methyl-d(3) kinetic isotope effects are similar to those associated with the nonmigrating methyl group in neopentyl ester solvolyses. These results are in agreement with the recently published structure of the 7-norbornyl cation calculated at the highest ab initio level which has confirmed its nonclassical nature as originally proposed by Winstein.

  DOI：

  10.1021/jo00102a033
• 作为产物：
  描述：

  7-氧代双环[2.2.1]庚烷-1-甲酰氯 生成 1-Chloro-7-norbornanone
  参考文献：
  名称：

  KIRMSE W.; SANDKUEHLER P., LIEBIGS ANN. CHEM., 1981, NO 8, 1394-1406

  摘要：

  DOI：