2-(4-chlorobutyl)cyclopentanone | 90722-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-chlorobutyl)cyclopentanone
• 英文别名: 2-(4-Chlorobutyl)cyclopentan-1-one
• CAS: 90722-22-8
• 化学式: C₉H₁₅ClO
• 分子量: 174.671
• InChiKey: QRLIAGXDKLMIOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  4
• 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：

  2-(4-chlorobutyl)cyclopentanone 在 吡啶 、 甲醇 、 三甲基氯硅烷 、 diethylzinc 、 sodium iodide 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 0.5h， 生成 5-(4-Chloro-butyl)-bicyclo[3.1.0]hexan-1-ol
  参考文献：
  名称：

  Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones

  摘要：

  Optically active alpha-methyl alpha-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme(R)-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00411-6
• 作为产物：
  描述：

  1-氯-4-碘丁烷 、 环戊酮二甲基腙 在 potassium dihydrogenphosphate 、 正丁基锂 、 亚磷酸 作用下， 生成 2-(4-chlorobutyl)cyclopentanone
  参考文献：
  名称：

  Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones

  摘要：

  Optically active alpha-methyl alpha-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme(R)-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00411-6

文献信息

• Sequenced reactions with samarium(II) iodide. Intermolecular ketyl-olefin coupling/intramolecular nucleophilic acyl substitution for the preparation of six-, seven-, and eight-membered carbocycles
  作者：Gary A Molander、Masakazu Sono

  DOI：10.1016/s0040-4020(98)00584-5

  日期：1998.8

  A samarium(II) iodide-promoted sequence consisting of an intermolecular ketyl-olefin coupling followed by an intramolecular nucleophilic acyl substitution is described. This process leads to functionalized six- to eight-membered monocyclic and bicyclic ring systems in moderate to good yields.

  描述了一种由碘化mar（II）促进的序列，该序列由分子间的酮基-烯烃偶联，然后进行分子内的亲核酰基取代组成。该过程导致以中等到良好的产率官能化的六元至八元单环和双环系统。
• Sequenced Reactions with Samarium(II) Iodide. A Complementary Annulation Process Providing Access to Seven-, Eight-, and Nine-Membered Carbocycles
  作者：Gary A. Molander、Fouzia Machrouhi

  DOI：10.1021/jo990216n

  日期：1999.5.1

  Samarium(II) iodide promotes an efficient one-pot annulation reaction between omega-iodo esters and 2-(omega-chloroalkyl)cycloalkanones. An initial intermolecular carbonyl addition reaction between the iodo ester and the ketone generates a lactone intermediate. The lactone undergoes a subsequent nucleophilic acyl substitution reaction with an organosamarium derived from the chloride. Nickel(II) iodide is an efficient catalyst for the first step of the process, and light is utilized to promote the second step. Seven-, eight-, and nine-membered rings can be accessed by this sequential dianionic process. This annulative approach to carbocycles is complementary to previously reported procedures.