1,1,4-Trichloro-1-(1-chloroethylsulfanyl)-3,3-dimethylbutan-2-one | 160193-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,4-Trichloro-1-(1-chloroethylsulfanyl)-3,3-dimethylbutan-2-one
• 英文别名: 1,1,4-trichloro-1-(1-chloroethylsulfanyl)-3,3-dimethylbutan-2-one
• CAS: 160193-96-4
• 化学式: C₈H₁₂Cl₄OS
• 分子量: 298.061
• InChiKey: UWAGHEALBYZJNR-UHFFFAOYSA-N

物化性质

• 沸点：
  286.887±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.369±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1,4-Trichloro-1-(1-chloroethylsulfanyl)-3,3-dimethylbutan-2-one 在 potassium tert-butylate 、 sodium ethanolate 、 四氯化钛 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 28.0h， 生成 Ethyl 1-(N-benzylamino)-2,2-dimethylcyclopropanecarboxylic ester
  参考文献：
  名称：

  Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Base-Induced Cyclization of .gamma.-Chloro-.alpha.-imino Esters

  摘要：

  beta-Chloro ketones were oxidatively transformed into alpha-keto carboxylic esters and condensed with primary amines in the presence of titanium(IV) chloride. Base-induced cyclization of the resulting gamma-chloro-alpha-imino esters, incorporating suitable N-substituents, led directly to 1-amino-2,2-dialkyl- cyclopropanecarboxylic ester derivatives via a 1,5-dehydrochlorination process. Syntheses of different N- and/or carboxyl-protected geminally (gem) dialkylated cyclopropane amino acids were developed, while access to the free alpha-amino acids is also given. The methodology used was further extended by reduction of the gamma-chloro-alpha-imino esters to functionalized gamma-chloro-alpha-amino esters,prior to ring closure, affording N-alkyl-gem-dialkyl-1-aminocyclopropanecarboxylic acid derivatives.

  DOI：

  10.1021/jo00102a022
• 作为产物：
  描述：

  2,2-Dimethyl-3-oxo-1-butyl trifluoroacetate 在 吡啶 、 磺酰氯 、 溴 、 sodium methylate 、 碳酸氢钠 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.08h， 生成 1,1,4-Trichloro-1-(1-chloroethylsulfanyl)-3,3-dimethylbutan-2-one
  参考文献：
  名称：

  Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Base-Induced Cyclization of .gamma.-Chloro-.alpha.-imino Esters

  摘要：

  beta-Chloro ketones were oxidatively transformed into alpha-keto carboxylic esters and condensed with primary amines in the presence of titanium(IV) chloride. Base-induced cyclization of the resulting gamma-chloro-alpha-imino esters, incorporating suitable N-substituents, led directly to 1-amino-2,2-dialkyl- cyclopropanecarboxylic ester derivatives via a 1,5-dehydrochlorination process. Syntheses of different N- and/or carboxyl-protected geminally (gem) dialkylated cyclopropane amino acids were developed, while access to the free alpha-amino acids is also given. The methodology used was further extended by reduction of the gamma-chloro-alpha-imino esters to functionalized gamma-chloro-alpha-amino esters,prior to ring closure, affording N-alkyl-gem-dialkyl-1-aminocyclopropanecarboxylic acid derivatives.

  DOI：

  10.1021/jo00102a022