5,5'-dibromo-2,2'-bis(methoxymethoxy)-3,3'-dinitro-1,1'-biphenyl | 1571076-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5'-dibromo-2,2'-bis(methoxymethoxy)-3,3'-dinitro-1,1'-biphenyl
• 英文别名: 5-Bromo-1-[5-bromo-2-(methoxymethoxy)-3-nitrophenyl]-2-(methoxymethoxy)-3-nitrobenzene
• CAS: 1571076-46-4
• 化学式: C₁₆H₁₄Br₂N₂O₈
• 分子量: 522.104
• InChiKey: MOUBNAKOTSJDNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,5'-dibromo-2,2'-bis(methoxymethoxy)-3,3'-dinitro-1,1'-biphenyl 在 吡啶 、 5%-palladium/activated carbon 、 palladium 10% on activated carbon 、 氢气 、 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， 20.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 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
• 作为产物：
  描述：

  5,5'-dibromo-2,2'-dihydroxybiphenyl 在 硝酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 5,5'-dibromo-2,2'-bis(methoxymethoxy)-3,3'-dinitro-1,1'-biphenyl
  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