(S)-N,N'-dibenzyl-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-N,N'-dibenzyl-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxamine
• 英文别名: (S)-N,N'-dibenzyl-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxamide；N-benzyl-4-[3-(benzylcarbamoyl)-2-hydroxynaphthalen-1-yl]-3-hydroxynaphthalene-2-carboxamide
• 化学式: C₃₆H₂₈N₂O₄
• 分子量: 552.629
• InChiKey: AVFYWIRRXFGCMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (S)-N,N'-dibenzyl-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxamine
  参考文献：
  名称：

  聚合物接枝的Ti-BINOL配合物作为手性催化剂在二乙基锌与醛的对映选择性加成中的制备及应用

  摘要：

  对映体BINOL已分别固定在BINOL的3和3,3'-位的氨基甲基化聚苯乙烯树脂上。所得的官能化聚合物4和7已经用作二乙基锌向醛的Ti催化对映选择性加成中的手性配体。与相同反应中的均相配体5和8相比，在某些情况下，聚合物负载的配体4和6具有更高的对映选择性。分析了配体的构象刚性，以说明结果。

  DOI：

  10.1016/s0040-4020(00)00260-x

文献信息

• Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides
  作者：Marco Caricato、Nerea Jordana Leza、Claudia Gargiulli、Giuseppe Gattuso、Daniele Dondi、Dario Pasini

  DOI：10.3762/bjoc.8.109

  日期：——

  Resolved, axially chiral binol scaffolds, which incorporate either methoxy or acetoxy functionalities in the 2,2' positions and carboxylic functionalities in the external 3,3' positions, were used as the source of chirality. Two of these binaphthyls are joined through amidation reactions using rigid diaryl amines of differing shapes, to give homochiral tetraamidic macrocycles. The recognition properties of

  我们报告了新型形状持久性、光学活性芳基酰胺大环的合成和表征，可以使用一锅法获得。解析的轴向手性二元醇支架，在 2,2' 位置结合甲氧基或乙酰氧基官能团，在外部 3,3' 位置结合羧基官能团，被用作手性来源。这些联萘中的两个通过使用不同形状的刚性二芳基胺的酰胺化反应连接，得到同手性四酰胺大环。已经分析了这些超分子受体的识别特性，结果表明对二羧酸根阴离子的结合亲和力的调节，结合模式的急剧变化取决于 2,2' 中官能团的空间和电子特征
• Polymer-Supported BINOL Ligand for the Titanium-Catalyzed Diethylzinc Addition to Aldehydes:  A Remarkable Positive Influence of the Support on the Enantioselectivity of the Catalyst
  作者：Xiao-Wu Yang、Jian-Heng Sheng、Chao-Shan Da、Heng-Shan Wang、Wu Su、Rui Wang、Albert S. C. Chan

  DOI：10.1021/jo990771p

  日期：2000.1.1

  A new polymer-supported BINOL (1,1'-Bi-2-naphthol) :was synthesized by coupling of aminomethyl polystyrene resin and (S)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylic acid. This new ligand was found to be more enantioselective for the asymmetric addition of diethylzinc to aldehydes than its "free" analog [Ti(BINOL)(PrO2)-Pr-i]. A range of 57-99% ee's as well as 78-97% yields was obtained, and: the electronic properties of the enantioselectivity were also observed.
• Preparation and Application of Polymer-Grafted Ti–BINOL Complexes as Chiral Catalysts in the Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Xiaowu Yang、Wu Su、Daxue Liu、Hengshan Wang、Jianheng Shen、Chaoshan Da、Rui Wang、Albert S.C. Chan

  DOI：10.1016/s0040-4020(00)00260-x

  日期：2000.5

  BINOL respectively. The resulting functionalized polymers 4 and 7 have been used as chiral ligands in the Ti-catalytic enantioselective addition of diethylzinc to aldehydes. Compared with the homogeneous ligands 5 and 8 in the same reaction, the polymer-supported ligands 4 and 6 gave, in some cases, higher enantioselectivity. The conformational inflexibility of the ligands was analyzed to illustrate the

  对映体BINOL已分别固定在BINOL的3和3,3'-位的氨基甲基化聚苯乙烯树脂上。所得的官能化聚合物4和7已经用作二乙基锌向醛的Ti催化对映选择性加成中的手性配体。与相同反应中的均相配体5和8相比，在某些情况下，聚合物负载的配体4和6具有更高的对映选择性。分析了配体的构象刚性，以说明结果。