1-(4-Brom-butyl)-cyclohexanon-(3) | 90976-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Brom-butyl)-cyclohexanon-(3)
• 英文别名: 3-(4-Bromobutyl)cyclohexanone；3-(4-bromobutyl)cyclohexan-1-one
• CAS: 90976-56-0
• 化学式: C₁₀H₁₇BrO
• 分子量: 233.148
• InChiKey: CUSQJDVTNPXGLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：

  1-(4-Brom-butyl)-cyclohexanon-(3) 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-(4-Bromobutyl)-2-cyclohexen-1-one 在 hydrido(triphenylphosphine)copper(I) hexamer 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以90%的产率得到1-(4-Brom-butyl)-cyclohexanon-(3)
  参考文献：
  名称：

  使用[（Ph 3 P）CuH] 6进行多官能团α，β-不饱和羰基化合物的共轭还原。与卤素，磺酸盐，γ-氧和硫取代基的相容性

  摘要：

  与有机铜酸盐共轭物添加和共轭物还原的标准方法相反，使用稳定的氢化铜（I）簇[[Ph 3 P）CuH] 6可以使取代在γ上的α，β-不饱和羰基化合物发生化学选择性共轭物还原离开团体的位置。另外，证明了共轭还原与有机卤化物和磺酸盐基团的相容性。

  DOI：

  10.1016/s0040-4039(00)89032-2

文献信息

• Rouessac,F.; Conia,J.-M., Bulletin de la Societe Chimique de France, 1961, p. 669
  作者：Rouessac,F.、Conia,J.-M.

  DOI：——

  日期：——
• KOENIG, THOMAS M.;DAEUBLE, JOHN F.;BRESTENSKY, DONNA M.;STRYKER, JEFFREY +, TETRAHEDRON LETT., 31,(1990) N3, C. 3237-3240
  作者：KOENIG, THOMAS M.、DAEUBLE, JOHN F.、BRESTENSKY, DONNA M.、STRYKER, JEFFREY +

  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.
• Conjugate reduction of polyfunctional α,β-unsaturated carbonyl compounds using [(Ph3P)CuH]6. Compatibility with halogen, sulfonate, and γ-oxygen and sulfur substituents
  作者：Thomas M. Koenig、John F. Daeuble、Donna M. Brestensky、Jeffrey M. Stryker

  DOI：10.1016/s0040-4039(00)89032-2

  日期：1990.1

  In contrast to organocuprate conjugate addition and standard methods for conjugate reduction, use of the stable copper(I) hydride cluster, [(Ph3P)CuH]6, allows chemoselective conjugate reduction of α,β-unsaturated carbonyl compounds substituted at the γ-position with leaving groups. In addition, the compatibility of the conjugate reduction with organic halides and sulfonate groups is demonstrated.

  与有机铜酸盐共轭物添加和共轭物还原的标准方法相反，使用稳定的氢化铜（I）簇[[Ph 3 P）CuH] 6可以使取代在γ上的α，β-不饱和羰基化合物发生化学选择性共轭物还原离开团体的位置。另外，证明了共轭还原与有机卤化物和磺酸盐基团的相容性。