1-(2-tert-butylphenyl)-6-hydroxypiperidin-2-one | 720712-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(2-tert-butylphenyl)-6-hydroxypiperidin-2-one
• CAS: 720712-05-0
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: PETZGGPSYIGPBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  1-(2-tert-butylphenyl)-6-hydroxypiperidin-2-one 在 三氯化铝 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 1,6-diphenylpiperidin-2-one
  参考文献：
  名称：

  Stereoselectivity in reactions of atropisomeric lactams and imides

  摘要：

  A range of reactions of cyclic lactam systems is described in which an atropisomeric C-N axis controls the stereochemical outcome of ring substitution or addition. In the case of enantiopure menthol adducts, substitution via N-acyliminium intermediates occurred with essentially complete control. However, the range of nucleophiles that participate in the reaction is very limited and at present the removal of the N-aryl substituent is problematic. A six-membered enamide is of moderate configurational stability and the axis exerts synthetically useful levels of control over enolate alkylations of the system. A novel Lewis acid mediated enamide arylation process was identified. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.100
• 作为产物：
  描述：

  2-叔丁基苯胺 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 1-(2-tert-butylphenyl)-6-hydroxypiperidin-2-one
  参考文献：
  名称：

  通过立体选择性环丙烷化反应合成 2-氮杂双环 [4.1.0] 庚烷

  摘要：

  在金属配合物催化的重氮化合物分解的帮助下，不饱和δ-内酰胺被环丙烷化。报道了对反应条件、立体化学结果和基团保护的研究。所得双环产物与生物活性化合物有关。转化为硫内酰胺有利于分离获得的不同异构体和去除保护基团。环丙烷化反应适用于多种重氮化合物。

  DOI：

  10.1002/ejoc.201000863

文献信息

• Light-Induced Enantiospecific 4π Ring Closure of Axially Chiral 2-Pyridones: Enthalpic and Entropic Effects Promoted by H-Bonding
  作者：Elango Kumarasamy、Josepha L. Jesuraj、Joseph N. Omlid、Angel Ugrinov、Jayaraman Sivaguru

  DOI：10.1021/ja203087a

  日期：2011.11.2

  Nonbiaryl axially chiral 2-pyridones were synthesized and employed for light-induced electrocyclic 4 pi ring closure leading to bicyclo-beta-lactam photoproducts in solution. The enantioselectivity in the photoproducts varied from 22 to 95% depending on the reaction temperature and the ability of the axially chiral chromophore to form intramolecular and/or intermolecular H-bonds with the solvent. On the basis of the differential activation parameters, entropic control of the enantiospecificity was observed for 2-pyridones lacking the ability to form H-bonds. Conversely, enthalpy played a significant role for 2-pyridones having the ability to form H-bonds.