(2S,2'R)-dibenzyl 2,2'-(((2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) | 1571076-48-6

• 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: (2S,2'R)-dibenzyl 2,2'-(((2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate)
• CAS: 1571076-48-6
• 化学式: C₄₂H₄₆N₄O₁₀
• 分子量: 766.848
• InChiKey: HYJUQZNYZSTKLR-ZPGRZCPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  56.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  154.2
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,2'R)-dibenzyl 2,2'-(((2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到(2S,2'R)-N,N'-(2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(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'-bis(methoxymethoxy)-3,3'-dinitro-1,1'-biphenyl 在 5%-palladium/activated carbon 、 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 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2S,2'R)-dibenzyl 2,2'-(((2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(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