(2R,3S)-(-)-ethyl 2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoate | 172821-16-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-(-)-ethyl 2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoate
• 英文别名: ethyl (2R,3S)-2-methyl-3-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoate
• CAS: 172821-16-8
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: IMKPYKYUSSWFAH-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(-)-ethyl 2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoate 在 lithium hydroxide monohydrate 、 水 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 16.17h， 以91%的产率得到(2R,3S)-(-)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid
  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：

  (S(S),2R,3S)-(+)-ethyl 2-methyl-3-(4-methylphenylsulfinamido)-3-phenylpropanoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(2R,3S)-(-)-ethyl 2-methyl-3-(4-methylphenylsulfonamido)-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).