(Z)-1-(ethylseleno)-1,4-diphenylbut-1-en-3-yne | 950894-26-5

• 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: (Z)-1-(ethylseleno)-1,4-diphenylbut-1-en-3-yne
• 英文别名: [(Z)-1-ethylselanyl-4-phenylbut-1-en-3-ynyl]benzene
• CAS: 950894-26-5
• 化学式: C₁₈H₁₆Se
• 分子量: 311.285
• InChiKey: ZILPTESHWALDJV-SDXDJHTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  (Z)-1-(ethylseleno)-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
• 作为产物：
  描述：

  二乙基二硒醚 、 1，4-二苯基丁二炔 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以71%的产率得到(Z)-1-(ethylseleno)-1,4-diphenylbut-1-en-3-yne
  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

• Butyltellurium Tribromide: A Suitable Electrophilic Source to Cyclization Reactions
  作者：Gilson Zeni、Diego Alves、Marina Prigol、Cristina Nogueira

  DOI：10.1055/s-2008-1042926

  日期：2008.4

  We present here our results of the electrophilic cyclization reaction of (Z)-chalcogenoenynes using butyltellurium tribromide as an electrophilic source. The cyclization reaction proceeded cleanly under mild reaction conditions and 3-(butyltellanyl)chalcogenophenes were formed in moderate to excellent yields. Subsequent, using these heterocycles as substrate to palladium-catalyzed cross-coupling reactions a new carbon-carbon bond was formed in good yields.

  我们在此介绍使用三溴化丁基碲作为亲电源对 (Z)- 卤代烯炔进行亲电环化反应的结果。环化反应在温和的反应条件下顺利进行，生成的 3-(丁基碲基)链烯的产率为中等到极好。随后，以这些杂环为底物，在钯催化下进行交叉偶联反应，以良好的收率形成了新的碳-碳键。
• 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.