methyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate | 681442-12-6

• 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: methyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate
• 英文别名: methyl (E)-2,4-dichloro-α-cyanocinnamate；Methyl (E)-2-cyano-3-(2,4-dichlorophenyl)acrylate；methyl (E)-2-cyano-3-(2,4-dichlorophenyl)prop-2-enoate
• CAS: 681442-12-6
• 化学式: C₁₁H₇Cl₂NO₂
• 分子量: 256.088
• InChiKey: CZSNOTKMRQXBIQ-XBXARRHUSA-N

物化性质

• 熔点：
  104 °C
• 沸点：
  387.3±42.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  二溴丙二酸二甲酯 、 methyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate 在 锌 作用下， 以 四氢呋喃 、 乙醚 、 六甲基磷酰三胺 为溶剂， 反应 1.08h， 以66%的产率得到trimethyl 3-(2,4-dichlorophenyl)-2-cyanocyclopropane-1,1,2-tricarboxylate
  参考文献：
  名称：

  Reaction of organozinc reagents formed in reaction of dibromomalonic acid dialkyl esters and zinc, with 2-arylmethylenemalonic acid dinitriles and 3-aryl-2-cyanopropenoic acid methyl esters

  摘要：

  Organozinc compounds, obtained from dibromomalonic acid dialkyl esters and zinc, react with 2-arylmethylmalonic acid dinitrites and 3-aryl-2-cyanopropenoic acid methyl esters forming 3-aryl-2,2-di-cyanocyclopropane-1,I-dicarboxylic acid dialkyl esters and 3-aryl-2-cyanocyclopropane-1,1,2-tricarboxylic acid trimethyl esters. H-1 and C-13 NMR, (3)J(CH) constants are considered.

  DOI：

  10.1134/s1070363206120152
• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 氰乙酸甲酯 在 ammonium dihydrogen phosphate 作用下， 以 水 为溶剂， 以90%的产率得到methyl (E)-2-cyano-3-(2,4-dichlorophenyl)-2-propenoate
  参考文献：
  名称：

  磷酸氢二铵在水中催化 Knoevenagel 缩合的新型、高效、绿色工艺

  摘要：

  摘要 在4 mol%的磷酸氢二铵存在下，各种芳香族和杂芳香族醛与氰基乙酸甲酯和乙酯、丙二腈和氰基乙酰胺等活性亚甲基化合物在水中搅拌顺利进行Knoevenagel缩合反应。反应在室温下短时间内进行，后处理程序非常简单，产率好到高。

  DOI：

  10.1080/00397910600781471

文献信息

• Cyclopropanation of Alkyl and Aryl 3-Aryl-2-cyanopropenoates with Bromine-containing Zinc Enolates Obtained from 1-Aryl-2,2-dibromoalkanones and Zinc
  作者：V. V. Shchepin、P. S. Silaichev、M. I. Vakhrin

  DOI：10.1007/s11178-006-0004-1

  日期：2005.11

  Zinc enolates prepared from 1-aryl-2,2-dibromoalkanones and zinc react with alkyl and aryl 3-aryl-2-cyanopropenoates affording alkyl and aryl 2-alkyl-3-aryl-2-aroyl-1-cyanocyclopropane-1-carboxylates.

  由1-芳基-2,2-二溴代烷酮和锌制备的锌烯醇化物与烷基和芳基3-芳基-2-氰基丙烯酸酯反应，生成烷基和芳基2-烷基-3-芳基-2-酰基-1-氰基环丙烷-1-羧酸酯。
• ——
  作者：Aicha El Maadi、Chance L. Matthiesen、Philip Ershadi、Jennifer Baker、Derrick M. Herron、Elizabeth M. Holt

  DOI：10.1023/a:1026155323394

  日期：——
• 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
  作者：V. V. Shchepin、Yu. G. Stepanyan、P. S. Silaichev、M. A. Ezhikova、M. I. Kodess

  DOI：10.1134/s1070428007070111

  日期：2007.7

  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.
• Novel, Efficient, and Green Procedure for the Knoevenagel Condensation Catalyzed by Diammonium Hydrogen Phosphate in Water
  作者：Saeed Balalaie、Morteza Bararjanian、Shohreh Hekmat、Peyman Salehi

  DOI：10.1080/00397910600781471

  日期：2006.8.1

  Abstract Knoevenagel condensation of various aromatic and heteroaromatic aldehydes with active methylene compounds like methyl and ethyl cyanoacetate, malononitrile, and cyanoacetamide proceeds smoothly with stirring in water in the presence of 4 mol% of diammonium hydrogen phosphate. The reactions were carried out at room temperature in short periods with very simple workup procedure and good to high

  摘要 在4 mol%的磷酸氢二铵存在下，各种芳香族和杂芳香族醛与氰基乙酸甲酯和乙酯、丙二腈和氰基乙酰胺等活性亚甲基化合物在水中搅拌顺利进行Knoevenagel缩合反应。反应在室温下短时间内进行，后处理程序非常简单，产率好到高。
• Reaction of organozinc reagents formed in reaction of dibromomalonic acid dialkyl esters and zinc, with 2-arylmethylenemalonic acid dinitriles and 3-aryl-2-cyanopropenoic acid methyl esters
  作者：V. V. Shchepin、Yu. G. Stepanyan、P. S. Silaichev、M. I. Kodess

  DOI：10.1134/s1070363206120152

  日期：2006.12

  Organozinc compounds, obtained from dibromomalonic acid dialkyl esters and zinc, react with 2-arylmethylmalonic acid dinitrites and 3-aryl-2-cyanopropenoic acid methyl esters forming 3-aryl-2,2-di-cyanocyclopropane-1,I-dicarboxylic acid dialkyl esters and 3-aryl-2-cyanocyclopropane-1,1,2-tricarboxylic acid trimethyl esters. H-1 and C-13 NMR, (3)J(CH) constants are considered.