2,2'-(2,2-dimethylpropane-1,3-diyldisulfinyl)dinaphthalene | 1312816-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-(2,2-dimethylpropane-1,3-diyldisulfinyl)dinaphthalene
• CAS: 1312816-40-2
• 化学式: C₂₅H₂₄O₂S₂
• 分子量: 420.596
• InChiKey: XWHQEFWLDOLNBA-ISILISOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (2,2-dimethylpropane-1,3-diyl)bis(naphthalen-2-ylsulfane) 在 bis(acetylacetonate)oxovanadium 、 (S)-2-(N-3',5'-diiodosalicylidene)-amino-3,3-dimethyl-1-butanol 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以38%的产率得到2,2'-(2,2-dimethylpropane-1,3-diyldisulfinyl)dinaphthalene
  参考文献：
  名称：

  Synthesis of C3- and C2-symmetric tris- and bis-sulfoxide ligands by asymmetric oxidation

  摘要：

  A series of tris- and bis-sulfoxides were synthesized by multiple asymmetric oxidation of the corresponding sulfides. High enantioselectivities were obtained based on Horeau-type amplification of selectivity. Naphthyl-substituted sulfoxides allowed for higher selectivity and greater ease of purification. These sulfoxides were tested as ligands in rhodium-catalyzed olefin hydroacylation and 1,4-addition of phenyl boronic acid to 2-cyclohexen-1-one. While no enantioinduction was observed in hydroacylation, up to 80% ee was obtained for a tris-sulfoxide and a bis-sulfoxide ligand in the 1,4-addition. Bis-sulfoxides with flexible backbones gave lower and inversed enantioselectivity, suggesting backbone rigidity plays a key role in enantioinduction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.023