di-tert-butyl 1-((R)-1-(tert-butoxycarbonyl)-3-(4-fluorophenyl)-2-oxoindolin-3-yl)hydrazine-1,2-dicarboxylate | 1257767-75-1

• 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-((R)-1-(tert-butoxycarbonyl)-3-(4-fluorophenyl)-2-oxoindolin-3-yl)hydrazine-1,2-dicarboxylate
• 英文别名: tert-butyl (3R)-3-(4-fluorophenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]-2-oxoindole-1-carboxylate
• CAS: 1257767-75-1
• 化学式: C₂₉H₃₆FN₃O₇
• 分子量: 557.619
• InChiKey: VAYOLDHNQLXAEW-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  tert-butyl 3-(4-fluorophenyl)-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87%的产率得到di-tert-butyl 1-((R)-1-(tert-butoxycarbonyl)-3-(4-fluorophenyl)-2-oxoindolin-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

• 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.