(5E)-2-methyldec-5-en-3-yn-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5E)-2-methyldec-5-en-3-yn-2-ol
• 英文别名: (E)-2-methyldec-5-en-3-yn-2-ol
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: UUNRJJUGCOPSQE-BQYQJAHWSA-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：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 iron(III)-acetylacetonate 哌啶 、 N-甲基吡咯烷酮 、 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 (5E)-2-methyldec-5-en-3-yn-2-ol
  参考文献：
  名称：

  Regiocontrol of the Palladium-Catalyzed Tin Hydride Addition to Z-Enynols:  Remarkable Z-Directing Effects

  摘要：

  [GRAPHICS]Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. The regioselectivity of the H-Sn bond addition was found to be controlled by the geometry of the double bond ( Z- or syn-directing effect) rather than the nature of its substituents. Exclusively alpha-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.

  DOI：

  10.1021/jo0701435

文献信息

• Stereoselective preparation of conjugated E-enynes from E-vinylic tellurides and terminal alkynes via Sonogashira cross-couplingElectronic supplementary information (ESI) available: spectroscopic data for all new compounds as well as detailed experimental procedures. See http://www.rsc.org/suppdata/ob/b4/b401059k/
  作者：Gilson Zeni、Diego Alves、Jesus M. Pena、Antonio L. Braga、Helio A. Stefani、Cristina W. Nogueira

  DOI：10.1039/b401059k

  日期：——

  E-Vinylic tellurides undergo a direct cross-coupling reaction with terminal alkynes in the presence of palladium(II)/CuI in Et(3)N at room temperature to give E-enynes in good yields. The methodology represents a general and efficient protocol for carrying out the synthesis of E-enynes under mild conditions with complete retention of configuration.

  在室温下，在Et（3）N中存在钯（II）/ CuI的情况下，E-Vinylic碲化物与末端炔烃进行直接交叉偶联反应，得到高收率的E-烯炔。该方法代表了在温和条件下完全保留构型进行E-烯炔的合成的通用而有效的方案。