(Z)-3-Phenyl-3-phenylamino-acrylic acid isopropyl ester | 217473-61-5

• 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)-3-Phenyl-3-phenylamino-acrylic acid isopropyl ester
• 英文别名: propan-2-yl (Z)-3-anilino-3-phenylprop-2-enoate
• CAS: 217473-61-5
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: ZMIPFAAWSZCXPZ-LGMDPLHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-Phenyl-3-phenylamino-acrylic acid isopropyl ester 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 isopropyl 3-oxo-3-(phenyl)propanoate
  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：

  N,1-diphenylethanimine 在 三氟化硼乙醚 、 sodium isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (Z)-3-Phenyl-3-phenylamino-acrylic acid isopropyl ester
  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

• Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction
  作者：Peng Sun、Jiaojiao Yang、Zirui Song、Yichao Cai、Yajie Liu、Chunxia Chen、Xin Chen、Jinsong Peng

  DOI：10.1055/s-0039-1690240

  日期：2020.1

  Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-(arylamino)acrylates

  从简单的苯胺和芳基丙酸酯酯开始，通过铜介导的顺序加氢胺化和交叉脱氢偶联（CDC）反应，开发了一种有效的一锅合成2-芳基吲哚-3-羧酸酯衍生物。苯胺在苯中的初始加氢胺化为芳基丙酸酯可在120°C下在CuCl 2 /菲咯啉，KMnO 4和KHCO 3存在下以立体选择性方式进行酯化（Z）-3-（芳基氨基）丙烯酸酯。因此，这些原位官能化的加合物可以在130°C的混合溶剂（苯/ DMSO 1：1）中直接进行芳族CH键的分子内氧化烯化反应，从而以良好或高收率获得多取代的吲哚。
• 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.