3-(4-Chlorobutyl)cyclohexan-1-one | 135699-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-Chlorobutyl)cyclohexan-1-one
• 英文别名: Cyclohexanone, 3-(4-chlorobutyl)-
• CAS: 135699-49-9
• 化学式: C₁₀H₁₇ClO
• 分子量: 188.697
• InChiKey: GUXJYOAHDYKBNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  3-(4-Chlorobutyl)cyclohexan-1-one 在 tris(dibenzoylmethano)iron(III) samarium diiodide 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 14.0h， 生成 Bicyclo<4.3.1>decan-1-ol
  参考文献：
  名称：

  A facile synthesis of bicyclo[m.n.1]alkan-1-ols. Evidence for organosamarium intermediates in the samarium(II) iodide promoted intramolecular Barbier-type reaction

  摘要：

  Samarium(II) iodide (SmI2) has been successfully employed as a reductive coupling agent for the intramolecular Barbier-type synthesis of bicyclo[m.n.1]alkan-1-ols. Thus, a variety of 3-(omega-iodoalkyl)cycloalkanones, upon treatment with SmI2 and a catalytic quantity of iron complex in tetrahydrofuran (THF), provide the title compounds in excellent yields. The reaction is quite general for the construction of diverse bicyclic ring systems, including the highly strained bicyclo[2.1.1]hexan-1-ol. In addition to exploring the synthetic utility of this reaction, studies have been performed which provide insight on the mechanistic details of the SmI2-promoted intramolecular Barbier-type synthesis. Compelling evidence for the intermediacy of organosamarium species has thus been gathered.

  DOI：

  10.1021/jo00013a008
• 作为产物：
  描述：

  3-丁-3-烯基环己烷-1-酮 、 盐酸 以68%的产率得到
  参考文献：
  名称：

  MOLANDER, GARY A.;MCKIE, JEFFREY A., J. ORG. CHEM., 56,(1991) N3, C. 4112-4120

  摘要：

  DOI：

文献信息

• A New Method for Synthesis of Functionalized Organozinc-Copper(I) Reagents and Their 1,4-Addition Reaction with Enones
  作者：Yulai Hu、Jianhua Yu、Shiyan Yang、Jin-Xian Wang、Yuanqi Yin

  DOI：10.1080/00397919808004854

  日期：1998.8

  Abstract The transmetalation of functionalized organozinc iodides with Cu(OAc)2 in THF provides a new convenient method for the preparation of functionalized organozinc-copper(I) reagents FG-RCu(OAc)ZnI which ultimately undergo 1,4-addition reaction with enones to give the products in good to excellent yields.

  摘要 功能化有机碘化物与 Cu(OAc)2 在 THF 中的金属转移为制备功能化有机锌铜 (I) 试剂 FG-RCu(OAc)ZnI 提供了一种新的便捷方法，该试剂最终与烯酮进行 1,4-加成反应。使产品具有良好的产量。
• Yang, Danfeng Huang Yihua; Wang, Jin-Xian; Hu, Yulai, Journal of Chemical Research - Part S, 2002, # 2, p. 79 - 81
  作者：Yang, Danfeng Huang Yihua、Wang, Jin-Xian、Hu, Yulai

  DOI：——

  日期：——
• MOLANDER, GARY A.;MCKIE, JEFFREY A., J. ORG. CHEM., 56,(1991) N3, C. 4112-4120
  作者：MOLANDER, GARY A.、MCKIE, JEFFREY A.

  DOI：——

  日期：——
• A facile synthesis of bicyclo[m.n.1]alkan-1-ols. Evidence for organosamarium intermediates in the samarium(II) iodide promoted intramolecular Barbier-type reaction
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00013a008

  日期：1991.6

  Samarium(II) iodide (SmI2) has been successfully employed as a reductive coupling agent for the intramolecular Barbier-type synthesis of bicyclo[m.n.1]alkan-1-ols. Thus, a variety of 3-(omega-iodoalkyl)cycloalkanones, upon treatment with SmI2 and a catalytic quantity of iron complex in tetrahydrofuran (THF), provide the title compounds in excellent yields. The reaction is quite general for the construction of diverse bicyclic ring systems, including the highly strained bicyclo[2.1.1]hexan-1-ol. In addition to exploring the synthetic utility of this reaction, studies have been performed which provide insight on the mechanistic details of the SmI2-promoted intramolecular Barbier-type synthesis. Compelling evidence for the intermediacy of organosamarium species has thus been gathered.