2-戊酮,3-乙基-3-(羟甲基)-(9CI) | 160193-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-戊酮,3-乙基-3-(羟甲基)-(9CI)
• 英文名称: 3-ethyl-3-hydroxymethyl-pentan-2-one
• 英文别名: 3-Aethyl-3-hydroxymethyl-pentan-2-on；3,3-Diaethyl-4-hydroxy-butan-2-on；3-Ethyl-3-(hydroxymethyl)pentan-2-one
• CAS: 160193-85-1
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: OFWALKINJXCRQV-UHFFFAOYSA-N

物化性质

• 沸点：
  219.5±13.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-戊酮,3-乙基-3-(羟甲基)-(9CI) 在 吡啶 、 磺酰氯 、 溴 、 sodium methylate 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.08h， 生成 1,1-Dichloro-3-(chloromethyl)-3-ethyl-1-ethylsulfanylpentan-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
• 作为产物：
  描述：

  3-乙基-2-戊酮 在 sodium carbonate 作用下， 反应 103.0h， 生成 2-戊酮,3-乙基-3-(羟甲基)-(9CI)
  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

文献信息

• Felkin, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1950, vol. 230, p. 304
  作者：Felkin

  DOI：——

  日期：——
• 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.