3-Phenylbenzoselenophene | 30439-49-7

• 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: 3-Phenylbenzoselenophene
• 英文别名: 3-Phenyl-1-benzoselenophene
• CAS: 30439-49-7
• 化学式: C₁₄H₁₀Se
• 分子量: 257.193
• InChiKey: BXAQZTUZHIKNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  15
• 可旋转键数：
  1
• 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

• 作为产物：
  描述：

  2-碘代苯甲酮 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 3-Phenylbenzoselenophene
  参考文献：
  名称：

  Free-radical homolytic substitution at selenium: an efficient method for the preparation of selenophenes

  摘要：

  Substituted and unsubstituted 1-(benzylseleno)-4-iodobut-3-en-2-ols 12 and 2-(benzylseleno)-1-(2-iodophenyl)ethanols 18 react smoothly with tris(trimethylsilyl)silane in benzene at 80-degrees-C (AIBN initiator) to afford selenophenes 16 and benzoselenophenes 21 in excellent yield. These reactions presumably involve intramolecular homolytic substitution by aryl and vinyl radicals 14 and 20 at the selenium atom with the expulsion of benzyl radical followed by facile dehydration to afford the aromatic selenophene ring system in each case. Competitive rate studies on the ring closure of the 2-[2-(benzylseleno)ethyl]phenyl radical 25 in the presence of tri-n-butyltin hydride to give 2,3-dihydrobenzo[b]selenophene (27) and 1-(benzylseleno)-2-phenylethane (28) provide a rate constant for ring closure (k(c)) of approximately 3 X 10(7) s-1 at 80-degrees-C. The determination of more accurate data is hampered by what we attribute to be the involvement of a slow, but competive nonradical process.

  DOI：

  10.1021/jo00073a021

文献信息

• Homolytic substitution at selenium: A convenient synthesis of benzoselenophenes
  作者：Carl H. Schiesser、Katarina Sutej

  DOI：10.1016/s0040-4039(00)61211-x

  日期：1992.8

  tris(trimethylylsilyl)silane (TTMSS) in benzene at 80° (AIBN initiator) to give benzo-[b]selenophenes (3) in 80–86% yield. Interestingly, when the parent selenide (6: R1 = R2 = H) is reacted with tri-n-butyltin hydride under similar conditions, 3-hydroxydihydrobenzo[b]selenophene (2: R1 = R2 = H) is isolated as the only product of radical cyclization.

  取代的2-苄基硒基-1-（2-碘苯基）乙醇（6）与苯中的三（三甲基硅烷基）硅烷（TTMSS）在80°（AIBN引发剂）下平稳反应，得到苯并[b]硒吩（3），在80-产率86％。有趣的是，当母体硒化物（6：R 1 = R 2 = H）在相似条件下与氢化三正丁基锡反应时，会分离出3-羟基二氢苯并[b]硒烯（2：R 1 = R 2 = H）作为自由基环化的唯一产物。
• Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation
  作者：Hiroki Iwamoto、Yuki Kojima、Kazutoshi Nishimura、Kosuke Yasui、Koji Hirano

  DOI：10.1021/acs.orglett.3c04033

  日期：2024.2.9

  ethanolamine, the corresponding benzoselenophene derivatives are obtained directly. The related synthesis of benzothiophene derivatives with sodium methanesulfinate is also possible with the unique assistance of the ball milling technique. The active species is considered to be a highly electrophilic chalcogen cation, which enables successive bond formation even at room temperature.

  已开发出 Tf 2 O 介导的 1,1-二芳基乙烯和联芳基化合物与甲硒酸的顺序 C-Se 键形成反应。用乙醇胺进行去甲基化后，直接得到相应的苯并硒吩衍生物。在球磨技术的独特帮助下，用甲亚磺酸钠进行苯并噻吩衍生物的相关合成也是可能的。该活性物质被认为是一种高度亲电子的硫族阳离子，即使在室温下也能连续形成键。
• Free-radical homolytic substitution at selenium: an efficient method for the preparation of selenophenes
  作者：Jennifer E. Lyons、Carl H. Schiesser、Katarina Sutej

  DOI：10.1021/jo00073a021

  日期：1993.10

  Substituted and unsubstituted 1-(benzylseleno)-4-iodobut-3-en-2-ols 12 and 2-(benzylseleno)-1-(2-iodophenyl)ethanols 18 react smoothly with tris(trimethylsilyl)silane in benzene at 80-degrees-C (AIBN initiator) to afford selenophenes 16 and benzoselenophenes 21 in excellent yield. These reactions presumably involve intramolecular homolytic substitution by aryl and vinyl radicals 14 and 20 at the selenium atom with the expulsion of benzyl radical followed by facile dehydration to afford the aromatic selenophene ring system in each case. Competitive rate studies on the ring closure of the 2-[2-(benzylseleno)ethyl]phenyl radical 25 in the presence of tri-n-butyltin hydride to give 2,3-dihydrobenzo[b]selenophene (27) and 1-(benzylseleno)-2-phenylethane (28) provide a rate constant for ring closure (k(c)) of approximately 3 X 10(7) s-1 at 80-degrees-C. The determination of more accurate data is hampered by what we attribute to be the involvement of a slow, but competive nonradical process.