4-cyano-2-methoxycarbonyl-3-phenylpenta-1,4-diene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-cyano-2-methoxycarbonyl-3-phenylpenta-1,4-diene
• 英文别名: Methyl 4-cyano-2-methylidene-3-phenylpent-4-enoate
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: AXEOGGWXZYFCIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyano-2-methoxycarbonyl-3-phenylpenta-1,4-diene 在 iron(III) chloride 、 溶剂黄146 作用下， 反应 5.0h， 以82%的产率得到3,5-Dimethylidene-4-phenylpiperidine-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
• 作为产物：
  描述：

  (Z)-methyl 2-(bromomethyl)-3-phenylacrylate 、 丙烯腈 在 三乙烯二胺 作用下， 反应 168.0h， 以67%的产率得到4-cyano-2-methoxycarbonyl-3-phenylpenta-1,4-diene
  参考文献：
  名称：

  Baylis–Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes

  摘要：

  A novel synthesis of functionalized 1,4-pentadienes via the reaction of acrylonitrile with allyl halides, derived from Baylis-Hillman adducts, in the presence of DABCO has been described, demonstrating for the first time the application of allyl halides as electrophiles in the Baylis-Hillman reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01886-4

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.
• Baylis–Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes
  作者：Deevi Basavaiah、Nagaswamy Kumaragurubaran、Duddu S Sharada

  DOI：10.1016/s0040-4039(00)01886-4

  日期：2001.1

  A novel synthesis of functionalized 1,4-pentadienes via the reaction of acrylonitrile with allyl halides, derived from Baylis-Hillman adducts, in the presence of DABCO has been described, demonstrating for the first time the application of allyl halides as electrophiles in the Baylis-Hillman reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.