(S)-2-(naphthalen-2-yl)-2,3-dihydroquinazolin-4(1H)-one | 1370352-22-9

• 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-(naphthalen-2-yl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: (S)-2-(2-naphthyl)-2,3-dihydroquinazolin-4(1H)-one；(2S)-2-naphthalen-2-yl-2,3-dihydro-1H-quinazolin-4-one
• CAS: 1370352-22-9
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: FPWOVEKUXZJCTE-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：

  2-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 (S)-2-(naphthalen-2-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

• Confinement‐Driven Enantioselectivity in 3D Porous Chiral Covalent Organic Frameworks
  作者：Bang Hou、Shi Yang、Kuiwei Yang、Xing Han、Xianhui Tang、Yan Liu、Jianwen Jiang、Yong Cui

  DOI：10.1002/anie.202013926

  日期：2021.3.8

  3D covalent organic frameworks (COFs) with well‐defined porous channels are shown to be capable of inducing chiral molecular catalysts from non‐enantioselective to highly enantioselective in catalyzing organic transformations. By condensations of a tetrahedral tetraamine and two linear dialdehydes derived from enantiopure 1,1′‐binaphthol (BINOL), two chiral 3D COFs with a 9‐fold or 11‐fold interpenetrated

  具有良好定义的多孔通道的3D共价有机骨架（COF）被证明能够催化手性分子催化剂从非对映选择性转变为高对映选择性，从而催化有机转化。通过将四面体四胺和两个对映体纯的1,1'-联萘酚（BINOL）衍生的线性二醛缩合，可以制备两个具有9倍或11倍互穿的类金刚石骨架的手性3D COF。与未固定化的酸相比，在管状通道内均匀分布的手性BINOL单元观察到了增强的布朗斯台德酸度。这促进了布朗斯台德酸催化醛和邻氨基苯甲酰胺的环缩合反应生成2,3-二氢喹唑啉酮。
• 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 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 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.