(R)-3-amino-3-phenyloxindole | 1257768-03-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-3-amino-3-phenyloxindole
• 英文别名: 3-amino-3-phenyl-2-oxoindole
• CAS: 1257768-03-8
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: DJQNKYGTPRQRMD-CQSZACIVSA-N

物化性质

• 沸点：
  426.2±45.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  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

文献信息

• Enantioselective Rhodium‐Catalyzed Addition of Arylboroxines to N‐Unprotected Ketimines: Efficient Synthesis of Cipargamin
  作者：Jinbin Zhu、Linwei Huang、Wei Dong、Naikai Li、Xingxin Yu、Wei‐Ping Deng、Wenjun Tang

  DOI：10.1002/anie.201910008

  日期：2019.11.4

  N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO-BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin

  通过使用具有低至1mol％的Rh负载的手性BIBOP型配体，首次实现了对映体选择性铑催化的芳基硼氧烷到N-未保护的酮亚胺的加成反应。通过使用WingPhos或PFBO-BIBOP作为配体，形成了一系列具有优异ee值和收率的手性α-三氟甲基-α，α-二芳基α-叔胺或3-氨基-3-芳基吲哚。该方法已经实现了西葫芦素的有效对映选择性合成。
• Organocatalytic Asymmetric α-Amination of Unprotected 3-Aryl and 3-Aliphatic Substituted Oxindoles using Di-tert-butyl Azodicarboxylate
  作者：Feng Zhou、Miao Ding、Yun-Lin Liu、Cui-Hong Wang、Cong-Bin Ji、Yi-Yu Zhang、Jian Zhou

  DOI：10.1002/adsc.201100379

  日期：2011.11

  The bifunctional quinine-derived thiourea catalyst 14 was found to catalyze the direct amination of unprotected 3-aryl and aliphatic substituted oxindoles with di-tert-butyl azodicarboxylate (DBAD) to construct a tetrasubstituted stereogenic carbon center at the C-3 position of oxindoles in good to excellent yield and enantioselectivity.

  发现双功能奎宁衍生的硫脲催化剂14催化了未保护的3-芳基和脂族取代的羟吲哚与偶氮二叔丁基二羧酸酯（DBAD）的直接胺化反应，从而在羟吲哚的C-3位置构建了一个四取代的立体碳中心。优良至优异的产率和对映选择性。