2,2,2-tris((2-naphthylthio)methyl)ethane | 201742-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,2-tris((2-naphthylthio)methyl)ethane
• 英文别名: 1,1,1-Tris(2-naphthylthiomethyl)ethane；2-[2-methyl-3-naphthalen-2-ylsulfanyl-2-(naphthalen-2-ylsulfanylmethyl)propyl]sulfanylnaphthalene
• CAS: 201742-29-2
• 化学式: C₃₅H₃₀S₃
• 分子量: 546.821
• InChiKey: VPBAHDZJIJZXAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,2-tris((2-naphthylthio)methyl)ethane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,2,2-tris((2-naphthylsulfinyl)methyl)ethane 、 2,2,2-tris((2-naphthylsulfinyl)methyl)ethane
  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
• 作为产物：
  描述：

  1,1,1-三氯甲基乙烷 、 2-萘硫醇 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.0h， 以91%的产率得到2,2,2-tris((2-naphthylthio)methyl)ethane
  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

文献信息

• Synthesis of C3- and C2-symmetric tris- and bis-sulfoxide ligands by asymmetric oxidation
  作者：Peter K. Dornan、Priscilla L. Leung、Vy M. Dong

  DOI：10.1016/j.tet.2011.02.023

  日期：2011.6

  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.