di-tert-butyl 1-(1-(tert-butoxycarbonyl)-2-oxo-3-(p-tolyl)indolin-3-yl)hydrazine-1,2-dicarboxylate | 1257767-66-0

• 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)-2-oxo-3-(p-tolyl)indolin-3-yl)hydrazine-1,2-dicarboxylate
• 英文别名: di-tert-butyl 1-((R)-1-(tert-butoxycarbonyl)-2-oxo-3-(p-tolyl)indolin-3-yl)hydrazine-1,2-dicarboxylate；tert-butyl (3R)-3-(4-methylphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]-2-oxoindole-1-carboxylate
• CAS: 1257767-66-0
• 化学式: C₃₀H₃₉N₃O₇
• 分子量: 553.656
• InChiKey: HGLXYSHMQBVMAQ-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl 3-(4-methylphenyl)-2-oxoindoline-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71%的产率得到di-tert-butyl 1-(1-(tert-butoxycarbonyl)-2-oxo-3-(p-tolyl)indolin-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

• Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts
  作者：Qiao-Wen Jin、Zhuo Chai、You-Ming Huang、Gang Zou、Gang Zhao

  DOI：10.3762/bjoc.12.72

  日期：——

  A highly enantioselective α-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by amino acids-derived chiral phosphine catalysts is reported. The corresponding products containing a tetrasubstituted carbon center attached to a nitrogen atom at the C-3 position of the oxindole were obtained in high yields and with up to 98% ee.

  报道了一种由氨基酸衍生的手性膦催化剂催化的含氮杂环化合物-偶氮二羧酸酯与3-取代氧吲哚的高对映选择性α-胺化反应。在此反应中，产物的C-3位置上的氮原子与四取代碳中心相连，产物收率高，对映体纯度可达98%。
• 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.