1,1,4-Trichloro-1-(ethylthio)-3,3-dimethyl-2-butanone | 146679-14-3

• 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-(ethylthio)-3,3-dimethyl-2-butanone
• 英文别名: 1,1,4-Trichloro-1-ethylsulfanyl-3,3-dimethylbutan-2-one
• CAS: 146679-14-3
• 化学式: C₈H₁₃Cl₃OS
• 分子量: 263.616
• InChiKey: UWHWXEONHJRXHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 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-(ethylthio)-3,3-dimethyl-2-butanone 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 sodium methylate 、 sodium ethanolate 、 四氯化钛 作用下， 以 甲醇 、 乙醚 、 正戊烷 为溶剂， 反应 83.0h， 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：

  4-chloro-1-(ethylthio)-3,3-dimethyl-2-butanone 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到1,1,4-Trichloro-1-(ethylthio)-3,3-dimethyl-2-butanone
  参考文献：
  名称：

  官能化甲基酮氧化转化为 α-酮羧酸酯

  摘要：

  摘要 通过金属离子辅助醇解相应的 β-酮-α, α-二氯烷基硫化物，将甲基酮氧化转化为 α-酮酯。

  DOI：

  10.1080/00397919208021144

文献信息

• Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Base-Induced Cyclization of .gamma.-Chloro-.alpha.-imino Esters
  作者：Marc Boeykens、Norbert De Kimpe、Kourosch Abbaspour Tehrani

  DOI：10.1021/jo00102a022

  日期：1994.11

  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.
• Oxidative Transformation of Functionalized Methyl Ketones into α-Ketocarboxylic Esters
  作者：Marc Boeykens、Norbert De Kimpe

  DOI：10.1080/00397919208021144

  日期：1992.12

  Abstract Methyl ketones are oxidatively transformed into α-keto esters by metal ion assisted alcoholysis of the corresponding β-keto-α, α-dichloroalkyl sulfides.

  摘要 通过金属离子辅助醇解相应的 β-酮-α, α-二氯烷基硫化物，将甲基酮氧化转化为 α-酮酯。