2-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one | 1374021-13-2

• 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: 2-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: (2S)-2-naphthalen-1-yl-2,3-dihydro-1H-quinazolin-4-one
• CAS: 1374021-13-2
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: XKEIBCWTOUEGSH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1-萘甲醛 在 (S)-3,3'-双(9-蒽基)-1,1'-联萘-2,2'-二基磷酸氢酯 、 硅酸四乙酯 作用下， 以 氯仿 为溶剂， 反应 101.0h， 生成 2-(naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  由亚胺和2-氨基苯甲酰胺催化不对称合成二氢喹唑啉酮

  摘要：

  利用亚胺和束缚的氮/氮亲核试剂，开发了前所未有的催化非对称合成含氨基的杂环化合物的方法。在10 mol％的手性磷酸存在下，一系列芳族，α，β-不饱和和脂族亚胺与2-氨基苯甲酰胺反应生成二氢喹唑啉酮，收率和收率良好。通过与手性磷酸和2-氨基苯甲酰胺的非键相互作用，亚胺N-取代基会极大地影响对映选择性。

  DOI：

  10.1002/adsc.201100849

文献信息

• Regulation of Chiral Phosphoric Acid Catalyzed Asymmetric Reaction through Crown Ether Based Host–Guest Chemistry
  作者：Jiadong Tang、Can Chen、Tao Hong、Zibin Zhang、Chunsong Xie、Shijun Li

  DOI：10.1021/acs.orglett.2c03091

  日期：2022.11.4

  in-depth intersection of supramolecular chemistry and asymmetric catalysis due to its unique advantages in building chiral catalyst libraries and regulating performance of catalysts. Herein, we combine crown ether based host–guest chemistry with chiral phosphoric acid mediated asymmetric catalysis to actualize the supramolecular regulation of catalytic asymmetric two-component tandem acetalization

  超分子不对称催化由于其在构建手性催化剂库和调节催化剂性能方面的独特优势而产生于超分子化学和不对称催化的深入交叉。在此，我们将基于冠醚的主客体化学与手性磷酸介导的不对称催化相结合，以实现催化不对称双组分串联缩醛化反应的超分子调控。与没有主客体相互作用的催化反应相比，添加碱金属客体后，产率提高了72%，对映选择性提高了13%，证明了这种超分子调控策略的巨大优势。
• 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.
• Highly Enantioselective Synthesis of Dihydroquinazolinones Catalyzed by SPINOL-Phosphoric Acids
  作者：Dan Huang、Xuejian Li、Fangxi Xu、Luhang Li、Xufeng Lin

  DOI：10.1021/cs400591u

  日期：2013.10.4

  The asymmetric condensation/amine addition cascade sequence of 2-aminobenzamides and aldehydes catalyzed by chiral spirocyclic SPINOL-phosphoric acids was realized. SPINOL-phosphoric acid 1j was found to be a general, highly enantioselective organocatalyst for such cascade reactions at room temperature, affording 2,3-dihydroquinazolinones in excellent yields (up to 99%) with good to excellent ee's (up to 98%). The best level of stereocontrol was obtained for aromatic aldehydes with an ortho substituent.
• Catalytic Asymmetric Synthesis of Dihydroquinazolinones from Imines and 2-Aminobenzamides
  作者：Dao-Juan Cheng、Yu Tian、Shi-Kai Tian

  DOI：10.1002/adsc.201100849

  日期：2012.4.16

  An unprecedented catalytic asymmetric synthesis of aminal‐containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles. In the presence of 10 mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β‐unsaturated, and aliphatic imines react with 2‐aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee.

  利用亚胺和束缚的氮/氮亲核试剂，开发了前所未有的催化非对称合成含氨基的杂环化合物的方法。在10 mol％的手性磷酸存在下，一系列芳族，α，β-不饱和和脂族亚胺与2-氨基苯甲酰胺反应生成二氢喹唑啉酮，收率和收率良好。通过与手性磷酸和2-氨基苯甲酰胺的非键相互作用，亚胺N-取代基会极大地影响对映选择性。