(+/-)-(Z)-1-(1H-1-imidazolyl)-3-phenyl-3-(1-phenylethylamino)-2-propen-1-one | 217473-41-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (+/-)-(Z)-1-(1H-1-imidazolyl)-3-phenyl-3-(1-phenylethylamino)-2-propen-1-one
• 英文别名: (Z)-1-imidazol-1-yl-3-phenyl-3-(1-phenylethylamino)prop-2-en-1-one
• CAS: 217473-41-1
• 化学式: C₂₀H₁₉N₃O
• 分子量: 317.39
• InChiKey: KWIYBZXTMCGAFD-RGEXLXHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(Z)-1-(1H-1-imidazolyl)-3-phenyl-3-(1-phenylethylamino)-2-propen-1-one 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 丙-2-烯-1-基3-羰基-3-苯基丙酸酯
  参考文献：
  名称：

  β-烯基氨基酸衍生物区域选择性合成的新方法

  摘要：

  在三氟化硼作为催化剂的存在下，通过酮亚胺与N，N'-羰基二咪唑的反应，开发了一种温和，简单而有效的途径来合成β-烯氨基咪唑碳酰衍生物3。也已经研究了3-向酯的转化。

  DOI：

  10.1016/s0040-4039(00)61664-7
• 作为产物：
  描述：

  (E)-1-phenyl-N-(1-phenylethylidene)ethanamine 、 N,N'-羰基二咪唑 在 lithium diisopropyl amide 作用下， 生成 (+/-)-(Z)-1-(1H-1-imidazolyl)-3-phenyl-3-(1-phenylethylamino)-2-propen-1-one
  参考文献：
  名称：

  Synthesis and Reactivity of New β-Enamino Acid Derivatives:  A Simple and General Approach to β-Enamino Esters and Thioesters

  摘要：

  A new strategy has been developed for the synthesis of several beta-enamino acid derivatives. N,N'-Carbonyldiimidazole has been used as C-acylating agent of methyl ketimines, providing a direct and simple route to new beta-enamino carbonyl imidazole derivatives 2. These derivatives 2 were cleanly and efficiently transformed into beta-enamino esters 4 (X = O) and thioesters 4 (X = S) by reaction with a great variety of alcohols and thiols, including tertiary ones. Alternative and complementary routes to compounds 4 were also investigated. In addition, beta-keto esters 6 have been obtained by mild acid hydrolysis of beta-enamino esters 4.

  DOI：

  10.1021/jo9809480

文献信息

• A new method for the regioselective synthesis of β-enamino acid derivatives
  作者：Santos Fustero、Ma Dolores Díaz、Raquel Pérez Carlón

  DOI：10.1016/s0040-4039(00)61664-7

  日期：1993.1

  A mild, simple and efficient route to β-enamino imidazole carbonilic derivatives 3 by reaction of ketimines with N,N′-carbonyl diimidazole in the presence of boron triflouride as catalyst has been developed. The conversion of 3 to esters has also been explored.

  在三氟化硼作为催化剂的存在下，通过酮亚胺与N，N'-羰基二咪唑的反应，开发了一种温和，简单而有效的途径来合成β-烯氨基咪唑碳酰衍生物3。也已经研究了3-向酯的转化。
• Synthesis and Reactivity of New β-Enamino Acid Derivatives:  A Simple and General Approach to β-Enamino Esters and Thioesters
  作者：Santos Fustero、Marta García de la Torre、Viviana Jofré,、Raquel Pérez Carlón、Antonio Navarro、Antonio Simón Fuentes、Juan Server Carrió

  DOI：10.1021/jo9809480

  日期：1998.11.1

  A new strategy has been developed for the synthesis of several beta-enamino acid derivatives. N,N'-Carbonyldiimidazole has been used as C-acylating agent of methyl ketimines, providing a direct and simple route to new beta-enamino carbonyl imidazole derivatives 2. These derivatives 2 were cleanly and efficiently transformed into beta-enamino esters 4 (X = O) and thioesters 4 (X = S) by reaction with a great variety of alcohols and thiols, including tertiary ones. Alternative and complementary routes to compounds 4 were also investigated. In addition, beta-keto esters 6 have been obtained by mild acid hydrolysis of beta-enamino esters 4.