3-(2-Brom-ethyl)-cycloheptanon-1 | 57337-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Brom-ethyl)-cycloheptanon-1
• 英文别名: 3-(2-Bromoethyl)cycloheptan-1-one
• CAS: 57337-75-4
• 化学式: C₉H₁₅BrO
• 分子量: 219.121
• InChiKey: DGVDSWPJPXBALH-UHFFFAOYSA-N

物化性质

• 沸点：
  283.2±13.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 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：

  3-(2-Brom-ethyl)-cycloheptanon-1 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 3-(2-碘乙基)环庚烷-1-酮
  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-vinylcycloheptan-1-one 在 氢溴酸 作用下， 以 正己烷 为溶剂， 生成 3-(2-Brom-ethyl)-cycloheptanon-1
  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

文献信息

• The Synthesis of Strained Methylene-bridged Bicyclic Olefins by the IntramolecularWittig Reaction
  作者：Konrad B. Becker

  DOI：10.1002/hlca.19770600111

  日期：1977.1.26

  A convenient synthesis of the strained methylene-bridged trans-cyclooctenes bicyclo[3.3.1]-1 (2)-nonene (1), bicyclo[4.2.1]-1(8)-nonene (2), and bicyclo[4.2.1]-1(2)-nonene (3) by the intramolecular Wittig reaction is described (see Schemes 1–4). The (3-oxocycloalkyl)alkyl-phosphonium bromides 20, 27 and 38 undergoing cyclization to the bridgehead olefins are formed by simple reaction sequences. The

  应变合成的亚甲基桥连反式环辛烯双环[3.3.1] -1（2）-壬烯（1），双环[4.2.1] -1（8）-壬烯（2）和双环[4.2 [1]描述了通过分子内Wittig反应的-1（2）-壬烯（3）（参见方案1-4）。的（3-氧代环）烷基鏻溴化物20，27和38经受环化到桥头烯烃通过简单的反应顺序形成。关于烯烃的应变，讨论了其光谱特性（IR，1 H-NMR，13 C-NMR和UV）。