di-tert-butyl 1-[1-(tert-butoxycarbonyl)-2-oxo-3-phenylindolin-3-yl]hydrazine-1,2-dicarboxylate | 1257767-60-4

• 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-phenylindolin-3-yl]hydrazine-1,2-dicarboxylate
• 英文别名: di-tert-butyl 1-((R)-1-(tert-butoxycarbonyl)-2-oxo-3-phenylindolin-3-yl)hydrazine-1,2-dicarboxylate；tert-butyl (3R)-3-[(2-methylpropan-2-yl)oxycarbonyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]-2-oxo-3-phenylindole-1-carboxylate
• CAS: 1257767-60-4
• 化学式: C₂₉H₃₇N₃O₇
• 分子量: 539.629
• InChiKey: PPTGXRQOEIICMB-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 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：
  7

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 1-[1-(tert-butoxycarbonyl)-2-oxo-3-phenylindolin-3-yl]hydrazine-1,2-dicarboxylate 在 盐酸 、 5% Rh/C 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 以63%的产率得到(R)-3-amino-3-phenyloxindole
  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
• 作为产物：
  描述：

  tert-butyl 2-oxo-3-phenylindoline-1-carboxylate 、 偶氮二甲酸二叔丁酯 在 (S)-(6-(3-((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， 反应 48.0h， 以94%的产率得到di-tert-butyl 1-[1-(tert-butoxycarbonyl)-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

• Design of Efficient Chiral Bifunctional Phase-Transfer Catalysts Possessing an Amino Functionality for Asymmetric Aminations
  作者：Suva Paria、Qi-Kai Kang、Miho Hatanaka、Keiji Maruoka

  DOI：10.1021/acscatal.8b03292

  日期：2019.1.4

  An efficient, chiral bifunctional phase-transfer catalyst with an intramolecular amino functionality has been designed and successfully applied to highly enantioselective amination of 3-aryloxindoles and 3-arylbenzofuran-2(3H)-ones with bis(adamantyl) azodicarboxylate. Optically active amination products were generally obtained in high yield with high enantioselectivity. The origin of stereoselectivity

  设计了一种具有分子内氨基官能团的高效手性双官能相转移催化剂，并将其成功地用于3-芳基羟吲哚和3-芳基苯并呋喃-2（3H）-与双（金刚烷基）偶氮二羧酸酯的高度对映选择性胺化。通常以高收率和高对映选择性获得光学活性胺化产物。通过DFT计算解释了立体选择性的起源。
• 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。