(S,S)-bis[2-(1-hydroxyethyl)phenyl] diselenide | 170379-93-8

• 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: (S,S)-bis[2-(1-hydroxyethyl)phenyl] diselenide
• 英文别名: (1S)-1-[2-[[2-[(1S)-1-hydroxyethyl]phenyl]diselanyl]phenyl]ethanol
• CAS: 170379-93-8
• 化学式: C₁₆H₁₈O₂Se₂
• 分子量: 400.238
• InChiKey: UXRATEPHZGNOGD-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  20
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-bis[2-(1-hydroxyethyl)phenyl] diselenide 在 溴 作用下， 以 甲醇 、 四氯化碳 、 乙醚 为溶剂， 反应 2.5h， 生成 (1S)-1-[2-[(2R)-2-methoxy-2-phenylethyl]selanylphenyl]ethanol
  参考文献：
  名称：

  Wirth, Thomas, Angewandte Chemie, 1995, vol. 107, # 16, p. 1872 - 1873

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-溴-Alpha-甲基苯甲醇 在 selenium 、 叔丁基锂 作用下， 生成 (S,S)-bis[2-(1-hydroxyethyl)phenyl] diselenide
  参考文献：
  名称：

  Asymmetric Addition Reactions with Optimized Selenium Electrophiles

  摘要：

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.

  DOI：

  10.1002/chem.19970031123

文献信息

• New and Efficient Chiral Selenium Electrophiles
  作者：Lars Uehlin、Gianfranco Fragale、Thomas Wirth

  DOI：10.1002/1521-3765(20020301)8:5<1125::aid-chem1125>3.0.co;2-i

  日期：2002.3.1

  New chiral diselenides were prepared in a few steps from readily available starting materials. The selenium electrophiles generated from these diselenides were used for the efficient stereoselective inter- and intramolecular functionalization of alkenes. The substitution pattern influences the stereoselectivities and protection of the hydroxy moiety in the chiral side chain led to increased selectivities

  从现有的起始原料中分几步制备新的手性二硒化物。从这些二硒化物生成的硒亲电子试剂用于烯烃的高效立体选择性分子间和分子内官能化。取代模式影响手性侧链中的立体选择性和羟基部分的保护，从而导致硒基化反应中选择性和产率的提高。在第二邻位的另外的取代基也是有利的。获得具有高达96％de的加成产物。在一定程度上也研究了亲核试剂对烯烃亚硒化反应的影响。
• Asymmetric Addition Reactions with Optimized Selenium Electrophiles
  作者：Thomas Wirth、Gianfranco Fragale

  DOI：10.1002/chem.19970031123

  日期：1997.11

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.
• Wirth, Thomas, Angewandte Chemie, 1995, vol. 107, # 16, p. 1872 - 1873
  作者：Wirth, Thomas

  DOI：——

  日期：——