4-(2,5-diphenyl-selenophen-3-yl)-2-methyl-but-3-yn-2-ol | 950894-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2,5-diphenyl-selenophen-3-yl)-2-methyl-but-3-yn-2-ol
• 英文别名: 4-(2,5-Diphenylselenophen-3-yl)-2-methylbut-3-yn-2-ol
• CAS: 950894-58-3
• 化学式: C₂₁H₁₈OSe
• 分子量: 365.333
• InChiKey: KUEVJHLLKVVASI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2,5-diphenyl-selenophen-3-yl)-2-methyl-but-3-yn-2-ol 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 3-Ethynyl-2,5-diphenylselenophene
  参考文献：
  名称：

  通过无铜 Sonogashira 交叉偶联反应合成 3-炔基硒酚衍生物

  摘要：

  在无助催化剂条件下，在 DMF 中催化量的 Pd(PPh3)2Cl2 存在下，以 Et3N 为碱，3-碘硒酚衍生物与几个末端炔烃发生直接的 Sonogashira 交叉偶联反应。这种交叉偶联反应在温和的条件下顺利进行，并使用炔丙醇和炔丙醚以及烷基、乙烯基和芳基炔烃进行，以良好至极好的产率提供相应的 3-炔基硒吩。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200700707
• 作为产物：
  描述：

  1，4-二苯基丁二炔 在 bis-triphenylphosphine-palladium(II) chloride sodium tetrahydroborate 、 碘 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.16h， 生成 4-(2,5-diphenyl-selenophen-3-yl)-2-methyl-but-3-yn-2-ol
  参考文献：
  名称：

  Electrophilic Cyclization of (Z)-Selenoenynes:  Synthesis and Reactivity of 3-Iodoselenophenes

  摘要：

  We present here our results of the electrophilic cyclization reaction of (Z)-selenoenynes with different electrophiles such as I-2, ICl, PhSeBr, and PhSeCl. The cyclization reaction proceeded cleanly under mild reaction conditions, and 3-substituted selenophenes were formed in moderate to excellent yields. We observed that the nature of solvent and structure of (Z)-selenoenyne were important to the cyclization reaction. In addition, the obtained 3-iodoselenophenes were readily transformed to more complex products using a metal-halogen exchange reaction with n-BuLi and trapping the intermediate formed with aldehydes, furnishing the desired secondary alcohols in good yields. Conversely, using the palladium or copper catalyzed cross-coupling reactions with terminal alkynes or alkyl alcohols, we were able to convert 3-iodoselenophene to Sonogashira or Ullmann type products, respectively, in good yields.

  DOI：

  10.1021/jo070835t

文献信息

• 3-Iodoselenophene derivatives: a versatile substrate for Negishi cross-coupling reaction
  作者：Ricardo F. Schumacher、Diego Alves、Ricardo Brandão、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1016/j.tetlet.2007.11.070

  日期：2008.1

  3-Iodoselenophene derivatives undergo a direct Negishi cross-coupling reaction with several organozinc compounds in the presence of a catalytic amount of Pd(PPh3)4 in THF at room temperature. This cross-coupling reaction proceeded cleanly under mild conditions and permitted the formation of polyaromatic compounds in good yields.

  在室温下，在THF中催化量的Pd（PPh 3）4存在下，3-碘硒醚衍生物与几种有机锌化合物直接进行Negishi交叉偶联反应。该交叉偶联反应在温和条件下干净地进行，并允许以高收率形成多芳族化合物。
• Electrophilic Cyclization of (<i>Z</i>)-Selenoenynes:  Synthesis and Reactivity of 3-Iodoselenophenes
  作者：Diego Alves、Cristiane Luchese、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1021/jo070835t

  日期：2007.8.31

  We present here our results of the electrophilic cyclization reaction of (Z)-selenoenynes with different electrophiles such as I-2, ICl, PhSeBr, and PhSeCl. The cyclization reaction proceeded cleanly under mild reaction conditions, and 3-substituted selenophenes were formed in moderate to excellent yields. We observed that the nature of solvent and structure of (Z)-selenoenyne were important to the cyclization reaction. In addition, the obtained 3-iodoselenophenes were readily transformed to more complex products using a metal-halogen exchange reaction with n-BuLi and trapping the intermediate formed with aldehydes, furnishing the desired secondary alcohols in good yields. Conversely, using the palladium or copper catalyzed cross-coupling reactions with terminal alkynes or alkyl alcohols, we were able to convert 3-iodoselenophene to Sonogashira or Ullmann type products, respectively, in good yields.
• Synthesis of 3-Alkynylselenophene Derivatives by a Copper-Free Sonogashira Cross-Coupling Reaction
  作者：Diego Alves、Joel S. dos Reis、Cristiane Luchese、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1002/ejoc.200700707

  日期：2008.1

  3-Iodoselenophene derivatives undergo direct Sonogashira cross-coupling reactions with several terminal alkynes in the presence of a catalytic amount of Pd(PPh3)2Cl2 in DMF with Et3N as the base under cocatalyst-free conditions. This cross-coupling reaction proceeded cleanly under mild conditions and was performed with propargylic alcohols and propargylic ethers, as well as alkyl, vinyl and aryl alkynes

  在无助催化剂条件下，在 DMF 中催化量的 Pd(PPh3)2Cl2 存在下，以 Et3N 为碱，3-碘硒酚衍生物与几个末端炔烃发生直接的 Sonogashira 交叉偶联反应。这种交叉偶联反应在温和的条件下顺利进行，并使用炔丙醇和炔丙醚以及烷基、乙烯基和芳基炔烃进行，以良好至极好的产率提供相应的 3-炔基硒吩。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)