5-tert-butyl-1-(2-hydroxy-1-(3,4,5-trimethoxyphenyl)ethyl)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-hydroxy-1-(3,4,5-trimethoxyphenyl)ethyl)azepan-2-one
• 英文别名: (5R)-5-tert-butyl-1-[(1R)-2-hydroxy-1-(3,4,5-trimethoxyphenyl)ethyl]azepan-2-one
• 化学式: C₂₁H₃₃NO₅
• 分子量: 379.497
• InChiKey: ZLAZWWUNVRHGMD-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-叔丁基环己酮 、 (+/-)-2-azido-1-(3,4,5-trimethoxyphenyl)ethanol 在 三氟化硼乙醚 、 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到5-tert-butyl-1-(2-hydroxy-1-(3,4,5-trimethoxyphenyl)ethyl)azepan-2-one
  参考文献：
  名称：

  叠氮化物介导的不对称环膨胀反应中的非键，有吸引力的阳离子-π相互作用

  摘要：

  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.

  DOI：

  10.1021/jo800222r

文献信息

• 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.