(S)-4-(4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)benzonitrile | 1370352-26-3

• 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)-4-(4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)benzonitrile
• 英文别名: 4-[(2S)-4-oxo-2,3-dihydro-1H-quinazolin-2-yl]benzonitrile
• CAS: 1370352-26-3
• 化学式: C₁₅H₁₁N₃O
• mdl: MFCD00276353
• 分子量: 249.272
• InChiKey: ZHVFWULFBNJVQA-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基苯甲酰胺 、 4-氰基苯甲醛 在 2,6-双[(3aR,8aS)-(+)-8H-茚[1,2-d]恶唑啉-2-基]吡啶 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(S)-4-(4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)benzonitrile
  参考文献：
  名称：

  Highly Enantioselective Synthesis of 2,3-Dihydroquinazolinones through Intramolecular Amidation of Imines

  摘要：

  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.

  DOI：

  10.1021/ol300518m

文献信息

• Enantioselective synthesis of dihydroquinazolinone derivatives catalyzed by a chiral organocatalyst
  作者：Siva Ayyanar、Ponmuthu Kottala Vijaya、Madhappan Mariyappan、Veeramanoharan Ashokkumar、Velu Sadhasivam、Sankar Balakrishnan、Chithiraikumar Chinnadurai、Sepperumal Murugesan

  DOI：10.1039/c7nj00538e

  日期：——

  2-aminobenzamide and aldehydes, catalyzed by a novel chiral organocatalyst, was realized. The organocatalyst was found to be very effective and highly enantioselective for such cascade reactions at room temperature, affording 2,3-dihydroquinazolinones in excellent yields (up to 99%) with enantiomeric excesses of up to 97%. The best level of stereocontrol was obtained for aromatic/aliphatic aldehydes with ortho

  实现了新型手性有机催化剂催化的2-氨基苯甲酰胺与醛类的不对称缩合/胺加成级联序列。发现有机催化剂对于这种在室温下的级联反应是非常有效的和高度对映选择性的，以优异的产率（高达99％）提供了2，3-二氢喹唑啉酮，对映体过量高达97％。对于具有邻位，对位或间位取代基的芳族/脂肪族醛，可获得最佳的立体控制水平。
• 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。
• 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.