bis-(Z)-β-styryl selenide | 67502-78-7

• 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: bis-(Z)-β-styryl selenide
• 英文别名: bis-(Z,Z)-styryl selenide；(z,z)-Distyryl selenide；[(Z)-2-[(Z)-2-phenylethenyl]selanylethenyl]benzene
• CAS: 67502-78-7
• 化学式: C₁₆H₁₄Se
• 分子量: 285.247
• InChiKey: RPQHJXXTYDPTTH-XSYHWHKQSA-N

物化性质

• 熔点：
  38-40 °C
• 沸点：
  402.5±38.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• 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：

  4-戊炔-1-醇 、 bis-(Z)-β-styryl selenide 在 1,2-双(二苯基膦)乙烷氯化镍 四氢吡咯 、 copper(l) iodide 作用下， 反应 22.0h， 以76%的产率得到(Z)-1-phenylhept-1-en-3-yn-7-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Enynes by Nickel-Catalyzed Cross-Coupling of Divinylic Chalcogenides with Alkynes

  摘要：

  (Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.

  DOI：

  10.1021/jo0261707
• 作为产物：
  描述：

  苯乙炔 在 sodium selenide 作用下， 以 丙醇 为溶剂， 以71%的产率得到bis-(Z)-β-styryl selenide
  参考文献：
  名称：

  Stereoselective Synthesis of Enynes by Nickel-Catalyzed Cross-Coupling of Divinylic Chalcogenides with Alkynes

  摘要：

  (Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.

  DOI：

  10.1021/jo0261707

文献信息

• Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol
  作者：Gelson Perin、Angelita Barcellos、Eduardo Luz、Elton Borges、Raquel Jacob、Eder Lenardão、Luca Sancineto、Claudio Santi

  DOI：10.3390/molecules22020327

  日期：——

  A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH₄, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z

  通过将硒化钠物质区域和立体选择性地加成到芳基炔烃上，已经开发了一种简单有效的制备二乙烯基硒化物的方案。亲核物质是利用PEG-400作为溶剂，从元素硒与NaBH 3的反应中原位产生的。通过一步步骤在60°C下在短时间内进行反应，以中等至极好的收率获得了几种二乙烯基硒化物，对（Z，Z）-异构体具有选择性。该方法扩展到碲，以良好的收率得到所需的二乙烯基碲化物。此外，双（3，5-二甲氧基苯乙烯基）硒化物3f与（4-甲氧基苯基）溴化镁5的铁催化的交叉偶联反应以57％的产率提供了白藜芦醇三甲醚6。
• Stereospecific synthesis of divinyl selenides nucleophilic substitutions of unactivated vinyl halides by vinyl selenide anions
  作者：Lorenzo Testaferri、Marcello Tiecco、Marco Tingoli、Donatella Chianelli

  DOI：10.1016/s0040-4020(01)87402-0

  日期：1986.1

  Vinyl alkyl selenides can be dealkylated by nucleophilic substitution or by electron transfer to give vinyl selenide anions which retain the configuration of the starting products. The same anions are also produced by electron transfer from vinyl acetyl selenides. The vinyl selenide anions react with vinyl halides, in DMF or DMA, to give divinyl selenides. These reactions occur with retention of configuration

  乙烯基烷基硒化物可通过亲核取代或通过电子转移脱烷基，得到保留起始产物构型的乙烯基硒化物阴离子。同样的阴离子也可以通过电子转移从乙烯基乙酰硒化物中产生。硒化乙烯基阴离子与卤化乙烯基在DMF或DMA中反应，生成二乙烯基硒化物。这些反应在保留构型的情况下发生，代表了未活化乙烯基卤化物亲核取代的新例子。
• TESTAFERRI, L.;TIECCO, M.;TINGOLI, M.;CHIANELLI, D., TETRAHEDRON, 1986, 42, N 1, 63-69
  作者：TESTAFERRI, L.、TIECCO, M.、TINGOLI, M.、CHIANELLI, D.

  DOI：——

  日期：——
• Stereoselective Synthesis of Enynes by Nickel-Catalyzed Cross-Coupling of Divinylic Chalcogenides with Alkynes
  作者：Claudio C. Silveira、Antonio L. Braga、Adriano S. Vieira、Gilson Zeni

  DOI：10.1021/jo0261707

  日期：2003.1.1

  (Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.