ethyl(R(S),2S)-(-)-2-[phenyl-(2-methylpropanesulfinylamino)methyl]acrylate | 1138342-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl(R(S),2S)-(-)-2-[phenyl-(2-methylpropanesulfinylamino)methyl]acrylate
• 英文别名: ethyl 2-[(S)-[[(R)-tert-butylsulfinyl]amino]-phenylmethyl]prop-2-enoate
• CAS: 1138342-23-0
• 化学式: C₁₆H₂₃NO₃S
• 分子量: 309.43
• InChiKey: MSKJVNAJCZNIFM-SPLOXXLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl(R(S),2S)-(-)-2-[phenyl-(2-methylpropanesulfinylamino)methyl]acrylate 在 [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate 、 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以83%的产率得到ethyl (2S,3R)-3-[[(R)-tert-butylsulfinyl]amino]-2-methyl-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
• 作为产物：
  描述：

  (R)-N-benzylidene-2-methylpropane-2-sulfinamide 、 丙炔酸乙酯 在 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 rochelle salt 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以65%的产率得到ethyl(R(S),2S)-(-)-2-[phenyl-(2-methylpropanesulfinylamino)methyl]acrylate
  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).