(S)-2-(4-nitrophenyl)-2,3-dihydroquinolin-4(1H)-one | 1417196-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-2-(4-nitrophenyl)-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 2-(4-nitrophenyl)-2,3-dihydroquinolin-4(1H)-one；(2S)-2-(4-nitrophenyl)-2,3-dihydro-1H-quinolin-4-one
• CAS: 1417196-14-5
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: CYHDZHXJULBVFW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氨基苯乙酮 、 对硝基苯甲醛 在 6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octaamino-6^A,6^B,6^C,6^D,6^E,6^F,6^G,6^H-octadeoxy-γ-cyclodextrin 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以97%的产率得到(S)-2-(4-nitrophenyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Per-6-amino-β-cyclodextrin as a Chiral Base Catalyst Promoting One-Pot Asymmetric Synthesis of 2-Aryl-2,3-dihydro-4-quinolones

  摘要：

  A highly efficient one-pot synthesis of enantiomerically enriched 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been carried out for the first time using per-6-ABCD as a supramolecular host, chiral base catalyst, and a reusable promoter to give the corresponding scaffold with high yield (up to 99%) and enantiomeric excess (up to 99%). The catalyst is recovered and reused without loss in its activity.

  DOI：

  10.1021/jo302173a

文献信息

• One-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones catalyzed by amino acid-derived sulfonamides
  作者：Haixing Zheng、Qi Liu、Saishuai Wen、Hua Yang、Yiming Luo

  DOI：10.1016/j.tetasy.2013.05.028

  日期：2013.8

  approach to the asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones using amino-acid derived sulfonamides as organocatalysts, which can be easily prepared starting from l-proline, l-alanine, and l-phenylalanine, has been developed in high yields (up to 92%) and with moderate to good enantioselectivities (up to 74% ee). Additionally, opposite enantioselectivities for primary and secondary amino acid sulfonamides

  使用氨基酸衍生的磺酰胺作为有机催化剂的有机催化方法，用于不对称合成2-芳基-2,3-二氢-4-喹诺酮，可以很容易地从l-脯氨酸，l-丙氨酸和l-苯丙氨酸开始制备，已开发出高收率（高达92％）和中等至良好的对映选择性（高达74％ee）的化合物。另外，还观察到伯和仲氨基酸磺酰胺具有相反的对映选择性。
• Per-6-amino-β-cyclodextrin as a Chiral Base Catalyst Promoting One-Pot Asymmetric Synthesis of 2-Aryl-2,3-dihydro-4-quinolones
  作者：Kuppusamy Kanagaraj、Kasi Pitchumani

  DOI：10.1021/jo302173a

  日期：2013.1.18

  A highly efficient one-pot synthesis of enantiomerically enriched 2-aryl-2,3-dihydroquinolin-4(1H)-ones has been carried out for the first time using per-6-ABCD as a supramolecular host, chiral base catalyst, and a reusable promoter to give the corresponding scaffold with high yield (up to 99%) and enantiomeric excess (up to 99%). The catalyst is recovered and reused without loss in its activity.