(E)-3-Methylene-4-nonen-2-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: (E)-3-Methylene-4-nonen-2-ol
• 英文别名: (E)-3-methylidenenon-4-en-2-ol
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: KDNGPRMVQAVKEU-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反-1-碘己烯 、 (3-hydroxy-1-buten-2-yl)tributylstannane 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以41%的产率得到(E)-3-Methylene-4-nonen-2-ol
  参考文献：
  名称：

  .beta.-Stannyl Allylic Alcohols through Photooxygenation (Schenck Reaction) of Vinylstannanes and Reduction of the Resulting Allylic Hydroperoxides: Synthesis and Selected Transformations

  摘要：

  beta-Stannyl allylic alcohols 2 were prepared regioselectively by photooxygenation (Schenck reaction) of the vinylstannanes 1 and subsequent;reduction of the resulting allylic hydroperoxides by sodium borohydride. This novel methodology makes the hitherto unknown oxyfunctionalized cyclic vinylstannanes conveniently accessible, which constitute valuable building blocks in organic synthesis. For example, palladium-catalyzed coupling of these vinylstannanes 2 with allylic and vinylic halides produced the P-substituted allylic alcohols 3 in good yields. Tin-lithium exchange directly on the oxyfunctionalized vinylstannanes 2 afforded the corresponding lithio dianions, which on reaction with aldehydes led to the allylic diols 4. Furthermore, iododestannylation of the beta-stannyl allylic alcohols 2 gave the respective vinyl iodides 5.

  DOI：

  10.1021/jo00089a010

文献信息

• Tandem Enyne Metathesis and Claisen Rearrangement:  A Versatile Approach to Conjugated Dienes of Variable Substitution Patterns
  作者：Daniel A. Clark、Amol A. Kulkarni、Kyle Kalbarczyk、Bryan Schertzer、Steven T. Diver

  DOI：10.1021/ja063132m

  日期：2006.12.1

  enolate Claisen rearrangement. This reaction sequence provided conjugated dienes of higher substitution pattern than that obtained through a cross-enyne metathesis alone. The Ireland-Claisen was conducted across both acyclic and cyclic dienes produced from cross-metathesis and methylene-free enyne metathesis, respectively. In the case of cyclodienes, the Ireland-Claisen rearrangement produced s-trans

  为了扩展钌卡宾促进的烯炔复分解的多功能性，它与爱尔兰酯烯醇克莱森重排相结合。该反应序列提供了比单独通过跨烯炔复分解获得的取代模式更高的共轭二烯。Ireland-Claisen 分别对由交叉复分解和无亚甲基烯炔复分解产生的无环和环状二烯进行。在环二烯的情况下，爱尔兰-克莱森重排产生 s-反式锁定二烯，该二烯经历了模式选择性的烯反应。爱尔兰-克莱森重排的串联、顺序使用也证明适用于源自手性炔丙醇的手性转移。最后，串联复分解/Ireland-Claisen 用于获得 4-取代-3,5-环己二烯二醇衍生物，是天然产物合成中有价值的手性中间体。这种周环反应与催化复分解反应的结合扩展了交叉复分解的多功能性，因为可以访问额外的二烯基序。
• .beta.-Stannyl Allylic Alcohols through Photooxygenation (Schenck Reaction) of Vinylstannanes and Reduction of the Resulting Allylic Hydroperoxides: Synthesis and Selected Transformations
  作者：Waldemar Adam、Peter Klug

  DOI：10.1021/jo00089a010

  日期：1994.5

  beta-Stannyl allylic alcohols 2 were prepared regioselectively by photooxygenation (Schenck reaction) of the vinylstannanes 1 and subsequent;reduction of the resulting allylic hydroperoxides by sodium borohydride. This novel methodology makes the hitherto unknown oxyfunctionalized cyclic vinylstannanes conveniently accessible, which constitute valuable building blocks in organic synthesis. For example, palladium-catalyzed coupling of these vinylstannanes 2 with allylic and vinylic halides produced the P-substituted allylic alcohols 3 in good yields. Tin-lithium exchange directly on the oxyfunctionalized vinylstannanes 2 afforded the corresponding lithio dianions, which on reaction with aldehydes led to the allylic diols 4. Furthermore, iododestannylation of the beta-stannyl allylic alcohols 2 gave the respective vinyl iodides 5.