(3E)-3-[(3-chlorophenyl)methylidene]piperidine-2,6-dione | 1171246-73-3

• 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: (3E)-3-[(3-chlorophenyl)methylidene]piperidine-2,6-dione
• CAS: 1171246-73-3
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: BYDCVNJNSYSCRQ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(3-Chlorophenyl)-hydroxymethyl]prop-2-enenitrile 、 原乙酸三乙酯 在 丙酸 、 iron(III) chloride 、 溶剂黄146 作用下， 反应 12.0h， 以67%的产率得到(3E)-3-[(3-chlorophenyl)methylidene]piperidine-2,6-dione
  参考文献：
  名称：

  A simple protocol for the synthesis of a piperidine-2,6-dione framework from Baylis–Hillman adducts

  摘要：

  3-Hydroxy-2-methylenealkanenitriles, the Baylis-Hillman alcohols, derived from various aldehydes and acrylonitrile, have been conveniently transformed into 3-arylidene(or alkylidene)piperidine-2,6-diones in an operationally simple one-pot multi-step process involving Johnson-Claisen (J-C) rearrangement, partial hydrolysis, and cyclization. Rearranged Baylis-Hillman alcohols, (E)-2-hydroxymethyl-3-arylprop-2-enenitriles, have been converted into 4-aryl-3-methylidenepiperidine-2,6-diones in a similar reaction sequence. 4-Aryl-3,5-dimethylidenepiperidine-2,6-dione derivatives have been synthesized from Baylis-Hillman compounds, 3-aryl-4-cyano-2-methoxycarbonylpenta-1,4-dienes, obtained via the Baylis-Hillman reaction of methyl (2Z)-2-(bromomethyl)-3-arylprop-2-enoates with acrylonitrile, in a one-pot process. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.038

文献信息

• A simple protocol for the synthesis of a piperidine-2,6-dione framework from Baylis–Hillman adducts
  作者：Deevi Basavaiah、Dandamudi V. Lenin、Badugu Devendar

  DOI：10.1016/j.tetlet.2009.03.038

  日期：2009.7

  3-Hydroxy-2-methylenealkanenitriles, the Baylis-Hillman alcohols, derived from various aldehydes and acrylonitrile, have been conveniently transformed into 3-arylidene(or alkylidene)piperidine-2,6-diones in an operationally simple one-pot multi-step process involving Johnson-Claisen (J-C) rearrangement, partial hydrolysis, and cyclization. Rearranged Baylis-Hillman alcohols, (E)-2-hydroxymethyl-3-arylprop-2-enenitriles, have been converted into 4-aryl-3-methylidenepiperidine-2,6-diones in a similar reaction sequence. 4-Aryl-3,5-dimethylidenepiperidine-2,6-dione derivatives have been synthesized from Baylis-Hillman compounds, 3-aryl-4-cyano-2-methoxycarbonylpenta-1,4-dienes, obtained via the Baylis-Hillman reaction of methyl (2Z)-2-(bromomethyl)-3-arylprop-2-enoates with acrylonitrile, in a one-pot process. (C) 2009 Elsevier Ltd. All rights reserved.