ethyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate | 7324-89-2

• 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: ethyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate
• 英文别名: (E)-ethyl 2-cyano-3-(2,4-dichlorophenyl)acrylate；2-cyano-3t-(2,4-dichloro-phenyl)-acrylic acid ethyl ester；2-Cyan-3t-(2,4-dichlor-phenyl)-acrylsaeure-aethylester；2-<2,4-Dichlor-benzyliden>-cyanessigsaeure-aethylester；Ethyl 2-cyano-3-(2,4-dichlorophenyl)acrylate；ethyl (E)-2-cyano-3-(2,4-dichlorophenyl)prop-2-enoate
• CAS: 7324-89-2；24393-45-1
• 化学式: C₁₂H₉Cl₂NO₂
• mdl: MFCD00178324
• 分子量: 270.115
• InChiKey: HDHAZBAICIKTCX-WEVVVXLNSA-N

物化性质

• 熔点：
  82-84°
• 沸点：
  398.4±42.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2,2-二溴-1-茚酮 、 ethyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate 在 锌 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 以67%的产率得到ethyl 2-cyano-3-(2,4-dichlorophenyl)-1'-oxo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-2-carboxylate
  参考文献：
  名称：

  Cyclopropanation of 2-arylmethylidenemalononitriles, alkyl 3-aryl-2-cyanoprop-2-enoates, and N-substituted 3-aryl-2-cyanoprop-2-enamides with bromine-containing zinc enolates

  摘要：

  Zinc enolates derived from 2,2-dibromoindan-1-one and 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one reacted with 2-arylmethylidenemalononitriles, alkyl 3-aryl-2-cyanoprop-2-enoates, and N-substituted 3-aryl-2-cyanoprop-2-enamides to give, respectively, 3-aryl-1'-oxo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-2-2-dicarbonitriles, 3-aryl-1'-oxo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-2,2-dicarbonitriles, alkyl 3-aryl-2-cyano-1'-oxo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-2-carboxylates, alkyl 3-aryl-2-cyano-1'-oxo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-2-carboxylates, and N-substituted 3-aryl-2-cyanol-1'-oxo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-2-carboxamides as a single diastereoisomer. The stereoconfiguration of the products was determined by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1134/s1070428007070111
• 作为产物：
  描述：

  2-cyano-3t-(2,4-dichloro-phenyl)-acrylic acid 在 盐酸 作用下， 生成 ethyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate
  参考文献：
  名称：

  Shah et al., Journal of the Indian Chemical Society, 1959, vol. 36, p. 54

  摘要：

  DOI：

文献信息

• Green and Efficient Knoevenagel Condensation Catalysed by a DBU Based ionic Liquid in Water
  作者：An-Guo Ying、Li-Min Wang、Le-Le Wang、Xin-Zhi Chen、Wei-Dong Ye

  DOI：10.3184/030823409x12616597939085

  日期：2010.1

  An efficient, clean and facile protocol for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalysed by task specific ionic liquid 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate in an aqueous medium has been developed. The reactions proceed at room temperature and high to excellent yields were afforded. The workup procedure is very simple. The ionic liquid could

  一种高效、清洁和简便的方案，用于在水性介质中由任务特定的离子液体 1,8-二氮杂双环 [5.4.0]-undec-7-en-8-ium 乙酸盐催化芳香醛与活性亚甲基化合物的 Knoevenagel 缩合反应。被开发。反应在室温下进行，并提供了高到极好的收率。处理程序非常简单。离子液体可以循环使用 10 次而其催化活性没有明显损失。
• Knoevenagel Condensation Catalyzed by Sodium Silicate Under Solvent-Free Conditions
  作者：Qing Liu、Yinfeng Han

  DOI：10.1080/10426507.2011.558034

  日期：2011.10

  Abstract Sodium silicate pentahydrate has been utilized as an efficient catalyst for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds to afford substituted olefins in yields of 80.6%∼98.9% under solvent-free conditions at room temperature within a short time. The advantages of this procedure are mild reaction conditions, excellent yields, cleaner reaction profiles

  摘要 五水硅酸钠已被用作芳香醛与活性亚甲基化合物的Knoevenagel缩合反应的有效催化剂，在室温、无溶剂条件下短时间内以80.6%~98.9%的收率得到取代烯烃。该程序的优点是反应条件温和、产率高、反应曲线更清晰、操作简单。图形概要
• A simple, efficient, and green protocol for Knoevenagel condensation in a cost-effective ionic liquid 2-hydroxyethlammonium formate without a catalyst
  作者：Anguo Ying、Huading Liang、Renhua Zheng、Changhua Ge、Huajiang Jiang、Chenglin Wu

  DOI：10.1007/s11164-011-0300-4

  日期：2011.7

  Knoevenagel condensation of aromatic aldehydes with active methylene compounds such as malononitrile, ethylcyanoacetate, and cyanoacetamide proceeded very smoothly in reusable and cheap ionic liquid 2-hydroxyethylammonium formate at room temperature in the absence of a catalyst. Compared to other reported ionic liquids, the ionic liquid 2-hydroxyethylammonium formate shows better potential in the applications on the industrial scale with its low cost and viscosity.

  芳香醛与活性亚甲基化合物（如马隆腈、乙基氰乙酸酯和氰乙酰胺）的Knoevenagel缩合在可重复使用且廉价的离子液体2-羟基乙基铵甲酸盐中，在室温下无催化剂的情况下进行得非常顺利。与其他报道的离子液体相比，离子液体2-羟基乙基铵甲酸盐在工业规模应用中显示出更好的潜力，具有低成本和低粘度的优势。
• Sodium Benzoate as a Green, Efficient, and Recyclable Catalyst for Knoevenagel Condensation
  作者：Qing Liu、Hong-Mei Ai

  DOI：10.1080/00397911.2011.574245

  日期：2012.10.15

  Abstract Sodium benzoate was utilized as a novel efficient and green catalyst for the Knoevenagel condensation of aldehydes with active methylene compounds such as ethyl cyanoacetate and malononitrile to afford substituted olefins through the conventional stirring or under ultrasounic irradiation. Improvements were observed by carrying out the reactions under ultrasound irradiation. The reaction proceeded

  摘要 苯甲酸钠是一种新型高效绿色催化剂，用于醛类与氰乙酸乙酯、丙二腈等活性亚甲基化合物的Knoevenagel缩合反应，通过常规搅拌或超声辐照得到取代烯烃。通过在超声辐射下进行反应观察到了改进。反应在室温温和条件下顺利进行，并在短时间内以极好的收率获得了产物：催化剂保持活性并且在长达四个反应循环中没有表现出显着的活性损失。图形概要
• Bifunctional phosphine-catalyzed cross-Rauhut–Currier/Michael/aldol condensation triple domino reaction: synthesis of functionalized cyclohexenes
  作者：Peizhong Xie、You Huang、Wenqing Lai、Xiangtai Meng、Ruyu Chen

  DOI：10.1039/c1ob05693j

  日期：——

  A novel bifunctional phosphine-catalyzed reaction was developed. Cross-Rauhut–Currier, Michael and aldol reactions were successfully combined into a domino process. This method offers a powerful approach to the construction of highly substituted cyclohexene skeletons.

  开发了一种新型双功能膦催化反应。交叉-劳胡特-库里尔（Cross-RauhutâCurrier）、迈克尔（Michael）和醛醇（ldol）反应被成功地组合成一个多米诺过程。这种方法为构建高度取代的环己烯骨架提供了一种强有力的方法。