1-(2-tert-butylphenyl)-piperidine-2,6-dione | 720712-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(2-tert-butylphenyl)-piperidine-2,6-dione
• 英文别名: 1-(2-Tert-butylphenyl)piperidine-2,6-dione
• CAS: 720712-04-9
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: LRENRRYOONNBGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-tert-butylphenyl)-piperidine-2,6-dione 在 三氯化铝 、 二异丁基氢化铝 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.25h， 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 N,N'-羰基二咪唑 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 1.0h， 生成 1-(2-tert-butylphenyl)-piperidine-2,6-dione
  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

文献信息

• Synthesis of 2-Azabicyclo[4.1.0]heptanes through Stereoselective Cyclopropanation Reactions
  作者：Irene Suárez del Villar、Ana Gradillas、Javier Pérez-Castells

  DOI：10.1002/ejoc.201000863

  日期：2010.10

  catalysed by metal complexes. A study of the reaction conditions, stereochemical outcome and group protection is reported. The resulting bicyclic products are related to bioactive compounds. Transformation into thiolactams facilitates the separation of the different isomers obtained and the removal of the protecting group. The cyclopropanation reaction works with diverse diazo compounds.

  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。
• A Convenient Synthesis of Hindered<i>N</i>-Aryl Substituted Cyclic Amines
  作者：Murthy R. Akula、George W. Kabalka

  DOI：10.1080/00397919808007182

  日期：1998.6

  An efficient and high yielding synthesis of N-substituted pyrrolidines and piperidines is described.
• Stereoselectivity in reactions of atropisomeric lactams and imides
  作者：D.Jonathan Bennett、Alexander J Blake、Paul A Cooke、Christopher R.A Godfrey、Paula L Pickering、Nigel S Simpkins、Matthew D Walker、Claire Wilson

  DOI：10.1016/j.tet.2004.01.100

  日期：2004.5

  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.
• 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.