3-chlorodifluoromethyl-3-phenylaminoacrylate | 144850-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chlorodifluoromethyl-3-phenylaminoacrylate
• 英文别名: Ethyl 3-anilino-4-chloro-4,4-difluorobut-2-enoate；ethyl 3-anilino-4-chloro-4,4-difluorobut-2-enoate
• CAS: 144850-63-5
• 化学式: C₁₂H₁₂ClF₂NO₂
• 分子量: 275.683
• InChiKey: SXWVHXQTCXRRRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 3-chlorodifluoromethyl-3-phenylaminoacrylate 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以84%的产率得到N-phenyl-2-chlorodifluoromethyl-3-ethoxycarbonyl-1-azabutadiene
  参考文献：
  名称：

  Unexpected Formation of Polysubstituted 1-Azabutadienes and 1,3-Dioxanes from the Reaction of 3-Fluoroalkyl-3-arylaminoacrylic Acid Esters with Formaldehyde

  摘要：

  The reaction of 3-fluoroalkyl-3-arylaminoacrylic acid esters with formaldehyde was described. In the presence of a catalytic amount of triethylamine, the reaction took place readily in acetonitrile at 70 degrees C to give the corresponding 2-fluoroalkyl-1-azabutadienes in good yields. cis-Fluoroalkylated 1,3-dioxanes were obtained predominantly when the aryl ring contained an electron-withdrawing group and the reaction was carried out at room temperature under catalysis of triethylamine and tetrabutylammonium bromide. A possible mechanism was proposed.

  DOI：

  10.1021/jo0477852

文献信息

• A novel and efficient synthesis of fluoroalkylated multifunctional 1,2,3,4-tetrahydropyrimidines
  作者：Fu-Lu Zhao、Jin-Tao Liu

  DOI：10.1016/j.jfluchem.2004.06.010

  日期：2004.12

  Fluoroalkylated multifunctional 1,2,3,4-tetrahydropyrimidines were synthesized in almost quantitative yields for the first time by the reaction of 3-fluoroalkyl-3-anilinoacrylic acid esters with primary amines and formaldehyde under mild conditions. (C) 2004 Elsevier B.V. All rights reserved.
• Unexpected Formation of Polysubstituted 1-Azabutadienes and 1,3-Dioxanes from the Reaction of 3-Fluoroalkyl-3-arylaminoacrylic Acid Esters with Formaldehyde
  作者：Fu-Lu Zhao、Jin-Tao Liu

  DOI：10.1021/jo0477852

  日期：2005.5.1

  The reaction of 3-fluoroalkyl-3-arylaminoacrylic acid esters with formaldehyde was described. In the presence of a catalytic amount of triethylamine, the reaction took place readily in acetonitrile at 70 degrees C to give the corresponding 2-fluoroalkyl-1-azabutadienes in good yields. cis-Fluoroalkylated 1,3-dioxanes were obtained predominantly when the aryl ring contained an electron-withdrawing group and the reaction was carried out at room temperature under catalysis of triethylamine and tetrabutylammonium bromide. A possible mechanism was proposed.