(S)-benzyl2-((2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)carbamoyl)pyrrolidine-1-carboxylate | 1571076-52-2

• 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)-benzyl2-((2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)carbamoyl)pyrrolidine-1-carboxylate
• CAS: 1571076-52-2
• 化学式: C₃₆H₃₉N₃O₉S
• 分子量: 689.786
• InChiKey: LAAXNDPPWFBPIF-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  141.73
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-benzyl2-((2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)carbamoyl)pyrrolidine-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以63%的产率得到(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
• 作为产物：
  描述：

  5,5'-Dibromo-2,2'-dihydroxy-3,3'-dinitrodiphenyl 在 吡啶 、 5%-palladium/activated carbon 、 sodium hydride 、 一水合肼 、 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 为溶剂， 反应 39.0h， 生成 (S)-benzyl2-((2,2'-bis(methoxymethoxy)-3'-(4-methylphenylsulfonamido)-[1,1'-biphenyl]-3-yl)carbamoyl)pyrrolidine-1-carboxylate
  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