1-(Bromoacetyl)-1-(chloromethyl)cyclohexane | 146446-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(Bromoacetyl)-1-(chloromethyl)cyclohexane
• 英文别名: 2-Bromo-1-[1-(chloromethyl)cyclohexyl]ethanone
• CAS: 146446-28-8
• 化学式: C₉H₁₄BrClO
• 分子量: 253.567
• InChiKey: JQILPVCVSPVALS-UHFFFAOYSA-N

物化性质

• 沸点：
  309.8±12.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(Bromoacetyl)-1-(chloromethyl)cyclohexane 以 甲醇 为溶剂， 反应 20.0h， 生成 4-methoxy-2-oxaspiro<4.5>dec-3-ene
  参考文献：
  名称：

  Synthesis of 4,4-Dialkyltetrahydro-3-furanones

  摘要：

  4,4-二烷基四氢-3-呋喃酮是通过在 sodium alkoxides 的作用下，环合 3,3-二烷基-1溴-4氯-2-丁酮，并随后对所得到的 3,3-二烷氧基-4,4-二烷基四氢呋喃进行水解而制备的。

  DOI：

  10.1055/s-1992-26316
• 作为产物：
  描述：

  乙酰基环己烷 在 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 四氯化钛 、 sodium carbonate 、 lithium chloride 作用下， 以 四氯化碳 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 161.0h， 生成 1-(Bromoacetyl)-1-(chloromethyl)cyclohexane
  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

• 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.
• Synthesis of 4,4-Dialkyltetrahydro-3-furanones
  作者：Marc Boeykens、Norbert De Kimpe

  DOI：10.1055/s-1992-26316

  日期：——

  4,4-Dialkyltetrahydro-3-furanones were prepared by ring closure of 3, 3-dialkyl-1-bromo-4-chloro-2-butanones under the influence of sodium alkoxides and subsequent aqueous hydrolysis of the resulting 3,3-dialkoxy-4,4-dialkyltetrahydrofurans.

  4,4-二烷基四氢-3-呋喃酮是通过在 sodium alkoxides 的作用下，环合 3,3-二烷基-1溴-4氯-2-丁酮，并随后对所得到的 3,3-二烷氧基-4,4-二烷基四氢呋喃进行水解而制备的。