di-tert-butyl 1-[1-(tert-butoxycarbonyl)-5-methoxy-2-oxo-3-phenylindolin-3-yl]hydrazine-1,2-dicarboxylate | 1257767-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: di-tert-butyl 1-[1-(tert-butoxycarbonyl)-5-methoxy-2-oxo-3-phenylindolin-3-yl]hydrazine-1,2-dicarboxylate
• 英文别名: di-tert-butyl 1-((R)-1-(tert-butoxycarbonyl)-5-methoxy-2-oxo-3-phenylindolin-3-yl)hydrazine-1,2-dicarboxylate；tert-butyl (3R)-5-methoxy-3-[(2-methylpropan-2-yl)oxycarbonyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]-2-oxo-3-phenylindole-1-carboxylate
• CAS: 1257767-63-7
• 化学式: C₃₀H₃₉N₃O₈
• 分子量: 569.655
• InChiKey: FMDYSUHQEXYXDH-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  tert-butyl 5-methoxy-2-oxo-3-phenylindoline-1-carboxylate 、 偶氮二甲酸二叔丁酯 在 (1S)-(6-(3-((4-((S)-hydroxy((2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinolin-6-yloxy)methyl)benzyloxy)quinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol 作用下， 以 甲苯 为溶剂， 以96%的产率得到di-tert-butyl 1-[1-(tert-butoxycarbonyl)-5-methoxy-2-oxo-3-phenylindolin-3-yl]hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Highly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts

  摘要：

  An enantioselective alpha-amination of aryl oxindoles catalyzed by a dimeric quinidine has been developed. The reaction is general, broad in substrate scope, and affords the desired products in good yields with good to excellent enantioselectivities. This study provides the first examples of a general organocatalytic method for the creation of nitrogen-containing, tetrasubstituted chiral centers at C-3 of various aryl oxindoles. Furthermore, new catalysts and insights into structural elements of the catalysts that significantly influence enantioselectivities are disclosed.

  DOI：

  10.1021/ol102493q

文献信息

• Bifunctional thiourea-modified polymers of intrinsic microporosity for enantioselective α-amination of 3-aryl-2-oxindoles in batch and flow conditions
  作者：Laura Martín、Alicia Maestro、José M. Andrés、Rafael Pedrosa

  DOI：10.1039/d0ob01373k

  日期：——

  Two novel polymers of intrinsic microporosity decorated with chiral thioureas have been used as recoverable organocatalysts in enantioselective α-amination of 3-aryl-substituted oxindoles, creating a quaternary stereocenter. Both catalysts were able to promote the reaction in excellent yields and good enantioselection. Catalyst II, with a pyridyl nucleus, was used in recycling experiments maintaining

  两种用手性硫脲修饰的具有内在微孔的新型聚合物已被用作可回收的有机催化剂，用于 3-芳基取代的羟吲哚的对映选择性 α-胺化，产生四元立体中心。两种催化剂都能够以优异的收率和良好的对映体选择促进反应。具有吡啶基核的催化剂II用于在不进行额外再活化的情况下保持活性的再循环实验，以及在允许以多克规模合成胺化产物的流动过程中。
• Highly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts
  作者：Tommy Bui、Gloria Hernández-Torres、Ciro Milite、Carlos F. Barbas

  DOI：10.1021/ol102493q

  日期：2010.12.17

  An enantioselective alpha-amination of aryl oxindoles catalyzed by a dimeric quinidine has been developed. The reaction is general, broad in substrate scope, and affords the desired products in good yields with good to excellent enantioselectivities. This study provides the first examples of a general organocatalytic method for the creation of nitrogen-containing, tetrasubstituted chiral centers at C-3 of various aryl oxindoles. Furthermore, new catalysts and insights into structural elements of the catalysts that significantly influence enantioselectivities are disclosed.