(S)-N-(2,2'-dihydroxy-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide | 1571076-54-4

• 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'-dihydroxy-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide
• 英文别名: (2S)-N-[2-hydroxy-3-[2-hydroxy-3-[(4-methylphenyl)sulfonylamino]phenyl]phenyl]pyrrolidine-2-carboxamide
• CAS: 1571076-54-4
• 化学式: C₂₄H₂₅N₃O₅S
• 分子量: 467.546
• InChiKey: SKURYPYIFPVKHR-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2'-二羟基联苯 在 吡啶 、 5%-palladium/activated carbon 、 palladium 10% on activated carbon 、 氢气 、 溴 、 硝酸 、 sodium hydride 、 对甲苯磺酸 、 一水合肼 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 75.0h， 生成 (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
• 作为试剂：
  描述：

  环己酮 、 对溴苯甲醛 在 (S)-N-(2,2'-dihydroxy-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)pyrrolidine-2-carboxamide 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 69.0h， 以83%的产率得到(2S,1R)-2-(hydroxy(4-bromophenyl)methyl)cyclohexan-1-one
  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