1,3-bis(naphthalen-2-ylthio)propane | 111220-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-bis(naphthalen-2-ylthio)propane
• 英文别名: 2-(3-Naphthalen-2-ylsulfanylpropylsulfanyl)naphthalene
• CAS: 111220-28-1
• 化学式: C₂₃H₂₀S₂
• 分子量: 360.544
• InChiKey: ZUOMEVYXBVQTLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis(naphthalen-2-ylthio)propane 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 1,3-bis(naphthalen-2-ylsulfinyl)propane 、 1,3-bis(naphthalen-2-ylsulfinyl)propane
  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：

  二(甲烷磺酸)1,3-丙二醇酯 、 2-萘硫醇 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以1.06 g的产率得到1,3-bis(naphthalen-2-ylthio)propane
  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

• Reactions SRN1: partie no 18. action de sulfanions derives de HS(CH2)nSH vis-a-vis des halo-1 et -2 naphtalenes
  作者：René Beugelmans、Hélène Ginsburg

  DOI：10.1016/s0040-4039(00)95742-3

  日期：1987.1
• BEUGELMANS R.; GINSBURG H., TETRAHEDRON LETT., 28,(1987) N 4, 413-414
  作者：BEUGELMANS R.、 GINSBURG H.

  DOI：——

  日期：——
• 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.