(S)-2-(4-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one | 1417196-18-9

• 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-methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one
• 英文别名: (2S)-2-(4-methoxyphenyl)-2,3-dihydro-1H-quinolin-4-one
• CAS: 1417196-18-9
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: VSIFUPGNXLTSLA-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氨基苯乙酮 、 4-甲氧基苯甲醛 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98%的产率得到(S)-2-(4-methoxyphenyl)-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

• Primary amino acid catalyzed asymmetric intramolecular Mannich reaction for the synthesis of 2-aryl-2,3-dihydro-4-quinolones
  作者：Buddhadeb Mondal、Subhas Chandra Pan

  DOI：10.1039/c4ob02146k

  日期：——

  Primary amino acids are found to be good enantioselective catalysts for the direct asymmetric Mannich reaction between 2-amino acetophenone and aldehydes. The 2-aryl-2,3-dihydro-4-quinoline products are obtained in moderate to good yields and good to high enantioselectivities with 10 mol% of the primary amino acid catalyst under mild reaction conditions.

  发现伯氨基酸是2-氨基苯乙酮与醛之间直接不对称曼尼希反应的良好对映选择性催化剂。在温和的反应条件下，以10摩尔％的伯氨基酸催化剂以中等至良好的收率和良好至高的对映选择性获得2-芳基-2,3-二氢-4-喹啉产物。
• Organocatalytic one-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones
  作者：Gao-Fei Pan、Li Su、Yan-Lei Zhang、Shi-Huan Guo、Yong-Qiang Wang

  DOI：10.1039/c6ra01247g

  日期：——

  A highly efficient organocatalytic one-pot enantioselective synthesis of (R)-2-aryl-2,3-dihydro-4-quinolones from o-aminoacetophenones and aryl aldehydes has been developed. The approach is characterized by being metal free, solvent free and protecting group free. A variety of 2-aryl-2,3-dihydro-4-quinolones could be obtained in good yields up to 99% ee.

  从邻氨基苯乙酮和芳基醛开发了一种高效的有机催化一锅对映选择性合成（R）-2-芳基-2,3-二氢-4-喹诺酮。该方法的特征在于不含金属，不含溶剂和不含保护基。可以以高达99％ee的高收率获得各种2-芳基-2,3-二氢-4-喹诺酮类化合物。
• 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.