isopropyl (S)-(-)-1-<(4-methylphenyl)sulfinyl>naphthalene-2-carboxylate | 153583-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: isopropyl (S)-(-)-1-<(4-methylphenyl)sulfinyl>naphthalene-2-carboxylate
• 英文别名: propan-2-yl 1-[(S)-(4-methylphenyl)sulfinyl]naphthalene-2-carboxylate
• CAS: 153583-26-7
• 化学式: C₂₁H₂₀O₃S
• 分子量: 352.454
• InChiKey: DHMWDKPACKSSPW-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-萘基溴化镁, 0.5M IN METHF 、 isopropyl (S)-(-)-1-<(4-methylphenyl)sulfinyl>naphthalene-2-carboxylate 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 isopropyl (S)-(-)-1,1'-binaphthyl-2-carboxylate
  参考文献：
  名称：

  Directed metalation/ligand coupling approach to the enantioselective synthesis of 1,1′-binaphthyls

  摘要：

  Introduction of a 2-isopropoxycarbonyl or 2-N,N-dimethylcarbamoyl group into homochiral 1-p-tolyl- or 1-t-butyl-sulfinylnaphthalenes, via directed metalation reaction, followed by ligand coupling reaction with 1-naphthylmagnesium bromide, furnished atropisomeric 1,1'-binaphthyls in 82-95% enantiomeric excess (e.e.).

  DOI：

  10.1016/s0957-4166(00)82215-6
• 作为产物：
  描述：

  (-)-(S)-1-naphthyl p-tolyl sulphoxide 、 氯甲酸异丙酯 在 lithium diisopropyl amide 作用下， 生成 isopropyl (S)-(-)-1-<(4-methylphenyl)sulfinyl>naphthalene-2-carboxylate
  参考文献：
  名称：

  Directed metalation/ligand coupling approach to the enantioselective synthesis of 1,1′-binaphthyls

  摘要：

  Introduction of a 2-isopropoxycarbonyl or 2-N,N-dimethylcarbamoyl group into homochiral 1-p-tolyl- or 1-t-butyl-sulfinylnaphthalenes, via directed metalation reaction, followed by ligand coupling reaction with 1-naphthylmagnesium bromide, furnished atropisomeric 1,1'-binaphthyls in 82-95% enantiomeric excess (e.e.).

  DOI：

  10.1016/s0957-4166(00)82215-6

文献信息

• Baker, Robert W.; Hockless, David C. R.; Pocock, Geoffrey R., Journal of the Chemical Society. Perkin transactions I, 1995, # 20, p. 2615 - 2630
  作者：Baker, Robert W.、Hockless, David C. R.、Pocock, Geoffrey R.、Sargent, Melvyn V.、Skelton, Brian W.、et al.

  DOI：——

  日期：——
• Directed metalation/ligand coupling approach to the enantioselective synthesis of 1,1′-binaphthyls
  作者：Robert W. Baker、Geoffrey R. Pocock、Melvyn V. Sargent、Edi Twiss (née Stanojevic)

  DOI：10.1016/s0957-4166(00)82215-6

  日期：1993.1

  Introduction of a 2-isopropoxycarbonyl or 2-N,N-dimethylcarbamoyl group into homochiral 1-p-tolyl- or 1-t-butyl-sulfinylnaphthalenes, via directed metalation reaction, followed by ligand coupling reaction with 1-naphthylmagnesium bromide, furnished atropisomeric 1,1'-binaphthyls in 82-95% enantiomeric excess (e.e.).