5-tert-butyl-1-(2-cyclohexyl-2-hydroxyethyl)azepan-2-one

• 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: 5-tert-butyl-1-(2-cyclohexyl-2-hydroxyethyl)azepan-2-one
• 英文别名: (5R)-5-tert-butyl-1-[(2S)-2-cyclohexyl-2-hydroxyethyl]azepan-2-one
• 化学式: C₁₈H₃₃NO₂
• 分子量: 295.466
• InChiKey: GMEWJFUKPIKDDG-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+/-)-2-azido-1-cyclohexylethanol 、 4-叔丁基环己酮 在 三氟化硼乙醚 、 氢氧化钾 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 5-tert-butyl-1-(2-cyclohexyl-2-hydroxyethyl)azepan-2-one 、 5-tert-butyl-1-(2-cyclohexyl-2-hydroxyethyl)azepan-2-one
  参考文献：
  名称：

  由有吸引力的阳离子-n相互作用介导的高度立体选择性扩环反应。

  摘要：

  Electrostatic control of leaving group stereochemistry leads to superior diastereoselectivity in an asymmetric ring expansion reaction.

  DOI：

  10.1002/anie.200801591

文献信息

• Highly Stereoselective Ring Expansion Reactions Mediated by Attractive Cation-n Interactions
  作者：Timothy Ribelin、Christopher E. Katz、Donna G. English、Sherriel Smith、Anna K. Manukyan、Victor W. Day、Benjamin Neuenswander、Jennifer L. Poutsma、Jeffrey Aubé

  DOI：10.1002/anie.200801591

  日期：2008.8.4

  Electrostatic control of leaving group stereochemistry leads to superior diastereoselectivity in an asymmetric ring expansion reaction.
• Nonbonded, Attractive Cation−π Interactions in Azide-Mediated Asymmetric Ring Expansion Reactions
  作者：Christopher E. Katz、Timothy Ribelin、Donna Withrow、Yashar Basseri、Anna K. Manukyan、Amy Bermudez、Christian G Nuera、Victor W. Day、Douglas R. Powell、Jennifer L. Poutsma、Jeffrey Aubé

  DOI：10.1021/jo800222r

  日期：2008.5.1

  The influence of attractive, nonbonded interactions on the reactions of 1,2- and 1,3-hydroxyalkyl azides with ketones has been investigated through experimental and computational means. A series of 1,3-hydroxyalkyl azides bearing electronically tuned aromatic groups at the 2 position were prepared and reacted along with several derivatives designed to conformationally restrict the rotational orientation of the aromatic substituent. These studies showed that a cation-pi interaction between an aryl moiety and an N-2(+) leaving group plays a role in determining the stereoselectivity of these reactions. A series of ab initio calculations supported this hypothesis. A computational and experimental analysis suggested a primarily steric model for the analogous reactions of substituted 2-azido-1-ethanol analogues.