(R(S),2S,3R)-(-)-ethyl 2-benzyl-3-(1,1-dimethylethylsulfinamido)-3-phenylpropanoate | 1138342-31-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R(S),2S,3R)-(-)-ethyl 2-benzyl-3-(1,1-dimethylethylsulfinamido)-3-phenylpropanoate
• 英文别名: ethyl (2S,3R)-2-benzyl-3-[[(R)-tert-butylsulfinyl]amino]-3-phenylpropanoate
• CAS: 1138342-31-0
• 化学式: C₂₂H₂₉NO₃S
• 分子量: 387.543
• InChiKey: FPAGNIQJLBQVEZ-OWOAZTCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-ethyl (R(S),2S)-(-)-2-[phenyl-(2-methylpropane-2-sulfinylamino)methyl]-3-phenylacrylate 在 [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate 、 氢气 作用下， 以 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、2.53 MPa 条件下， 反应 72.0h， 以79%的产率得到(R(S),2S,3R)-(-)-ethyl 2-benzyl-3-(1,1-dimethylethylsulfinamido)-3-phenylpropanoate
  参考文献：
  名称：

  Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines). Asymmetric Synthesis of anti-α-Alkyl β-Amino Esters

  摘要：

  Addition of vinylaluminum NMO reagents to N-(p-toluenesufinyl)- and N-(2-methypropanesulfinyl)-derived sulfinimines gives N-sulfinyl aza-Morita-Baylis-Hillman products (dr = 7:1 to 12:1) that result from addition of the reagent from the least hindered direction. Hydrogenation of the aza-MBH adducts with a Rh(I) catalyst affords anti-alpha-substituted N-sulfinyl-beta-amino esters in good yield and high dr (10:1 to 21:1).

  DOI：

  10.1021/jo9001504

文献信息

• Vinylaluminum Addition to Sulfinimines (<i>N</i>-Sulfinyl Imines). Asymmetric Synthesis of <i>anti</i>-α-Alkyl β-Amino Esters
  作者：Franklin A. Davis、Hui Qiu、Minsoo Song、Narendra V. Gaddiraju

  DOI：10.1021/jo9001504

  日期：2009.4.3

  Addition of vinylaluminum NMO reagents to N-(p-toluenesufinyl)- and N-(2-methypropanesulfinyl)-derived sulfinimines gives N-sulfinyl aza-Morita-Baylis-Hillman products (dr = 7:1 to 12:1) that result from addition of the reagent from the least hindered direction. Hydrogenation of the aza-MBH adducts with a Rh(I) catalyst affords anti-alpha-substituted N-sulfinyl-beta-amino esters in good yield and high dr (10:1 to 21:1).