(S)-N-(2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide | 1571076-53-3

• 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: (S)-N-(2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide
• CAS: 1571076-53-3
• 化学式: C₂₈H₃₃N₃O₇S
• 分子量: 555.652
• InChiKey: VSGGSFRWHGFXTL-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  124.22
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以63%的产率得到(S)-N-(2,2'-dihydroxy-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Design, Synthesis and Organocatalysis of 2,2′-Biphenol-Based Prolinamide Organocatalysts in the Asymmetric Direct Aldol Reaction in Water

  摘要：

  In this work, 2,2-biphenol-based prolinamide water-compatible C-2- and C-1-symmetrical organocatalysts were synthesized with the use of enantiopure N-Cbz-(S)-proline as chiral source. Under the optimal reaction conditions, the C-1-symmetrical organocatalyst performed efficiently in the direct aldol reactions in water, thus delivering the desired aldol adducts in high yields (up to 100% yield) with excellent stereocontrol (up to 97:3 dr and 98% ee). The observed stereochemical outcome of the direct aldol reactions in water was interpreted by the proposed transition state.

  DOI：

  10.1055/s-0033-1339928
• 作为产物：
  描述：

  2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diamine 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 (S)-N-(2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Design, Synthesis and Organocatalysis of 2,2′-Biphenol-Based Prolinamide Organocatalysts in the Asymmetric Direct Aldol Reaction in Water

  摘要：

  In this work, 2,2-biphenol-based prolinamide water-compatible C-2- and C-1-symmetrical organocatalysts were synthesized with the use of enantiopure N-Cbz-(S)-proline as chiral source. Under the optimal reaction conditions, the C-1-symmetrical organocatalyst performed efficiently in the direct aldol reactions in water, thus delivering the desired aldol adducts in high yields (up to 100% yield) with excellent stereocontrol (up to 97:3 dr and 98% ee). The observed stereochemical outcome of the direct aldol reactions in water was interpreted by the proposed transition state.

  DOI：

  10.1055/s-0033-1339928