(2S,2'R)-N,N'-(2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(pyrrolidine-2-carboxamide) | 1571076-49-7

• 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)-N,N'-(2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(pyrrolidine-2-carboxamide)
• CAS: 1571076-49-7
• 化学式: C₂₆H₃₄N₄O₆
• 分子量: 498.579
• InChiKey: UJGLUYVDTQRVDI-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  119.18
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,2'R)-N,N'-(2,2'-bis(methoxymethoxy)-[1,1'-biphenyl]-3,3'-diyl)bis(pyrrolidine-2-carboxamide) 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(2S,2'R)-N,N'-(2,2'-dihydroxy-[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'-dihydroxy-3,3'-dinitrodiphenyl 在 5%-palladium/activated carbon 、 palladium 10% on activated carbon 、 氢气 、 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， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 (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