1-benzylseleno-2-(2-iodophenyl)propan-2-ol | 144428-06-8

• 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: 1-benzylseleno-2-(2-iodophenyl)propan-2-ol
• 英文别名: 1-Benzylselanyl-2-(2-iodophenyl)propan-2-ol
• CAS: 144428-06-8
• 化学式: C₁₆H₁₇IOSe
• 分子量: 431.175
• InChiKey: ZUVGFASRPBJHBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-benzylseleno-2-(2-iodophenyl)propan-2-ol 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 苯 为溶剂， 以82%的产率得到3-methylbenzo[b]selenophene
  参考文献：
  名称：

  硒的均质取代：苯并硒吩的便捷合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)61211-x
• 作为产物：
  描述：

  2'-碘苯乙酮 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 5.6h， 生成 1-benzylseleno-2-(2-iodophenyl)propan-2-ol
  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

• Toward Novel Antioxidants:  Preparation of Dihydrotellurophenes and Selenophenes by Alkyltelluride-Mediated Tandem S_RN1/S_Hi Reactions¹
  作者：Lars Engman、Melissa J. Laws、Jonas Malmström、Carl H. Schiesser、Lisa M. Zugaro

  DOI：10.1021/jo9907235

  日期：1999.9.1

  distributions similar to those observed for reactions involving n-BuTeNa. Lithium or sodium phenyltellurolate returned only starting materials from these reaction mixtures. The 2-[2-(n-butyltelluro)-1-hydroxy-1-methyl]ethylphenyl radical (14) is estimated to cyclize with k(c) = 5 x 10(8) s(-)(1) at 25 degrees C. The tandem S(RN)1/S(H)i sequence has been applied to the preparation of the antioxidant analogues, 5-hydroxy-2

  1-（2-碘苯基）-1-甲基环氧乙烷（12）与2当量的正丁基碲铝酸钠（n-BuTeNa）的反应，是由四氢化二正丁基硼氢化钠在THF中的硼氢化钠还原生成的，得到2， 3-二氢-3-羟基-3-甲基苯并[b] tellurophene（13）的产率为62％，以及少量的1-（n-丁基碲基）-2-苯基-2-丙醇（27）。该转化大概涉及串联的S（RN）1 / S（H）i序列。1-（苄基硒基）-2-苯基-2-丙醇（5a，R = Me）和1-烯丙氧基-2-碘苯（15）的相似反应得到2,3-二氢-3-羟基-3-甲基苯并[b]分别是]硒烯（17，74％）和3-（正丁基碲基）甲基-2,3-二氢苯并[b]呋喃（18，50％）。通过将碲直接插入所需的烷基锂中生成的烷基碲酸锂，碲上的叔丁基或叔丁基或叔丁基取代提供的产物分布与涉及正丁基萘的反应观察到的产物分布相似。苯基碲酸锂或钠仅从这些反应混合物中返回原料。估计2-
• 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。
• Intramolecular homolytic substitution at tellurium: Preparation of a dihydrotellurophene by alkyltelluride-mediated SRN1/SHi reactions
  作者：Melissa J. Laws、Carl H. Schiesser

  DOI：10.1016/s0040-4039(97)10239-8

  日期：1997.12

  Reaction of 1-methyl-1-(2-iodophenyl)oxirane (4) with two equivalents of sodium butyltelluroate (NaTeBu), generated throught the sodium borohydride reduction of dibutylditelluride, in THF, affords 2,3-dihydro-3-hydroxy-3-methylbenzo[b]tellurophene (6) in 57% yield, together with 1-(butyltelluro)-2-phenyl-2-propanol (7, 7%). This transformation presumably involves a tandem S(RN)1/S(H)i sequence which was investigated further through the reactions of 1-(benzylseleno)-2-phenyl-2-propanol (2, R-1 = Me; R-2 = H) and 1-allyloxy-2-iodobenzene (9) with sodium butyltelluroate under similar conditions. Mechanistic and kinetic implications are discussed. (C) 1997 Elsevier Science Ltd.
• 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.