1-((R)-2-Methyl-propane-2-sulfinyl)-naphthalene-2-carboxylic acid isopropyl ester | 153583-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((R)-2-Methyl-propane-2-sulfinyl)-naphthalene-2-carboxylic acid isopropyl ester
• 英文别名: propan-2-yl 1-[(R)-tert-butylsulfinyl]naphthalene-2-carboxylate
• CAS: 153583-27-8
• 化学式: C₁₈H₂₂O₃S
• 分子量: 318.437
• InChiKey: AVADHGAGKICTRN-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-萘基溴化镁, 0.5M IN METHF 、 1-((R)-2-Methyl-propane-2-sulfinyl)-naphthalene-2-carboxylic acid isopropyl ester 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 (R)-(+)-N,N-dimethyl-1,1'-binaphthyl-2-carboxamide
  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_S)-(-)-menthyl 1-naphthalenesulfinate 在 正丁基锂 作用下， 以 甲苯 为溶剂， 生成 1-((R)-2-Methyl-propane-2-sulfinyl)-naphthalene-2-carboxylic acid isopropyl ester
  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

• 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.).