2,5-diphenyl-3-iodoselenophene | 950894-38-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2,5-diphenyl-3-iodoselenophene
• 英文别名: 3-iodo-2,5-diphenylselenophene
• CAS: 950894-38-9
• 化学式: C₁₆H₁₁ISe
• 分子量: 409.128
• InChiKey: QQUNSKIRQZIPBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,5-diphenyl-3-iodoselenophene 在 正丁基锂 、 水 作用下， 以 正己烷 为溶剂， 反应 0.17h， 以97%的产率得到2,5-diphenylselenophene
  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
• 作为产物：
  描述：

  (Z)-1-(methylseleno)-1,4-diphenylbut-1-en-3-yne 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以90%的产率得到2,5-diphenyl-3-iodoselenophene
  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

• 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)
• 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。
• Green synthesis of halogenated thiophenes, selenophenes and benzo[b]selenophenes using sodium halides as a source of electrophilic halogens
  作者：Tanay Kesharwani、Krystal A. Giraudy、Jordan L. Morgan、Cory Kornman、Abayomi D. Olaitan

  DOI：10.1016/j.tetlet.2017.01.007

  日期：2017.2

  Herein, we report the first synthesis of chlorinated benzo[b]selenophenes via environmentally friendly electrophilic chlorocyclization reaction using "table salt" as a source of "electrophilic chlorine" and ethanol as a solvent. In addition, the synthesis of diverse halogenated heterocycles, including 3-chloro, 3-bromo and 3-iodo thiophenes, selenophenes, and benzo[b]selenophenes was successfully accomplished

  在此，我们报道了使用“食盐”作为“亲电子氯”的来源，并使用乙醇作为溶剂，通过环保的亲电子氯环化反应，首次合成了氯化苯并[b]硒代苯。另外，在相同的环境友好的反应条件下，成功地完成了包括3-氯，3-溴和3-碘噻吩，硒烯和苯并[b]硒烯在内的各种卤代杂环的合成。与其他先前报道的反应相比，该方法具有多种优势，因为它在温和的反应条件下采用简单的起始化合物，环境友好的溶剂，乙醇和无毒的无机试剂，从而提高了产品收率。
• Palladium-Catalyzed Cross-Coupling Reaction of 3-Iodoselenophenes with Boronic Acids
  作者：Gilson Zeni、Daniela Barancelli、Diego Alves、Patrícia Prediger、Eluza Stangherlin、Cristina Nogueira

  DOI：10.1055/s-2007-992383

  日期：2008.1

  The Suzuki cross-coupling of 3-iodoselenophenes with boronic acids in the presence of catalytic amount of palladium salt is described. This cross-coupling reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron-donating, and neutral substituents, furnishing the correspondents products in moderate to good yields.

  描述了在催化量的钯盐存在下 3-碘硒酚与硼酸的 Suzuki 交叉偶联。这种交叉偶联反应在温和的条件下干净地进行，并用带有吸电子、给电子和中性取代基的芳基硼酸进行，以中等至良好的产率提供相应的产物。
• A study on the cellular and cytotoxic effects of S and Se heterocycles on the myeloid leukemia cell line PLB-985
  作者：Niccole Auld、Krystal Flood、Tanay Kesharwani、Peter J. Cavnar

  DOI：10.1080/10426507.2022.2085272

  日期：2022.8.3