(Z)-6-(3-methoxyphenyl)-5-hexen-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-6-(3-methoxyphenyl)-5-hexen-1-ol
• 英文别名: (Z)-6-(3-methoxyphenyl)hex-5-en-1-ol
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: OOBBWDKBJDAXEN-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-己炔-1-醇 、 3-碘苯甲醚 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex indium(III) chloride 、 三乙基硼 、 二异丁基氢化铝 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以99%的产率得到(Z)-6-(3-methoxyphenyl)-5-hexen-1-ol
  参考文献：
  名称：

  Trans-Hydrometalation of Alkynes by a Combination of InCl₃ and DIBAL-H:  One-Pot Access to Functionalized (Z)-Alkenes

  摘要：

  Triethylborane-induced hydrometalation of alkynes proceeds in an anti manner to afford the corresponding (Z)-alkenylmetal compounds stereoselectively, where dichloroindium hydride would play a key role. A variety of functional groups including hydroxy, carbonyl, and carboxy groups were tolerant under the reaction conditions. Following iodolysis and cross-coupling reaction of the (Z)-alkenylmetal species show the usefulness of this strategy.

  DOI：

  10.1021/ol026401w

文献信息

• Triethylborane-Mediated Hydrogallation and Hydroindation:  Novel Access to Organogalliums and Organoindiums
  作者：Kazuaki Takami、Satoshi Mikami、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/jo0344790

  日期：2003.8.1

  Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.
• <i>Trans</i>-Hydrometalation of Alkynes by a Combination of InCl₃ and DIBAL-H:  One-Pot Access to Functionalized <i>(Z)</i>-Alkenes
  作者：Kazuaki Takami、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol026401w

  日期：2002.8.1

  Triethylborane-induced hydrometalation of alkynes proceeds in an anti manner to afford the corresponding (Z)-alkenylmetal compounds stereoselectively, where dichloroindium hydride would play a key role. A variety of functional groups including hydroxy, carbonyl, and carboxy groups were tolerant under the reaction conditions. Following iodolysis and cross-coupling reaction of the (Z)-alkenylmetal species show the usefulness of this strategy.