(S)-2-phenethyl-2,3-dihydroquinazolin-4(1H)-one | 1370352-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-2-phenethyl-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-phenethyl-2,3-dihydroquinazolin-4(1H)-one；(2S)-2-(2-phenylethyl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 1370352-30-9
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: WMTGARVXUJDDKB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丙醛 、 2-氨基苯甲酰胺 在 (4S)-2-[3-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)-5-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]-4-phenyl-4,5-dihydro-1,3-oxazole 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以85%的产率得到(S)-2-phenethyl-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Highly enantioselective synthesis of dihydroquinazolinones through Sc(OTf)3-catalyzed intramolecular amidation of imines

  摘要：

  A Sc(OTf)(3)-catalyzed intramolecular amidation of imines with a novel fluorous bis(oxazolines) as ligand is presented. The corresponding chiral dihydroquinazolinones were obtained in 76-94% yield with enantioselectivities up to 98%. The fluorous ligand can be easily recovered and reused at least three times without significant loss of enantioselectivity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.11.008

文献信息

• Highly Enantioselective Synthesis of 2,3-Dihydroquinazolinones through Intramolecular Amidation of Imines
  作者：Muthuraj Prakash、Venkitasamy Kesavan

  DOI：10.1021/ol300518m

  日期：2012.4.6

  Enantioselective synthesis of 2,3-dihydroquinazolinones (DHOZs) was accomplished using readily available Sc(III)-inda-pybox as the catalyst. This is the first report on the metal catalyzed asymmetric intramolecular amidation of imines to synthesize DHQs.
• Investigation of the Enantioselective Synthesis of 2,3-Dihydroquinazolinones Using Sc(III)-inda-pybox
  作者：Venkitasamy Kesavan、Muthuraj Prakash、Samydurai Jayakumar

  DOI：10.1055/s-0033-1339288

  日期：——

  Derivatives of 2,3-dihydroquinazolinones (2,3-DHQZs) are prized for their prevalent pharmaceutical applications. Although there are potential applications, methods available for the enantioselective synthesis of these valuable compounds are scarce, since the chiral aminal center is prone to racemization. We have overcome the difficulties in the catalytic enantioselective synthesis of 2,3-DHQZs using Sc(III)-inda-pybox as a catalyst, in a process with a broad substrate scope.
• Highly enantioselective synthesis of dihydroquinazolinones through Sc(OTf)3-catalyzed intramolecular amidation of imines
  作者：Tao Deng、Hongjun Wang、Chun Cai

  DOI：10.1016/j.jfluchem.2014.11.008

  日期：2015.1

  A Sc(OTf)(3)-catalyzed intramolecular amidation of imines with a novel fluorous bis(oxazolines) as ligand is presented. The corresponding chiral dihydroquinazolinones were obtained in 76-94% yield with enantioselectivities up to 98%. The fluorous ligand can be easily recovered and reused at least three times without significant loss of enantioselectivity. (C) 2014 Elsevier B.V. All rights reserved.