(S)-2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroquinazolin-4(1H)-one | 1133972-41-4

• 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-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: (2S)-2-(1,3-benzodioxol-5-yl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 1133972-41-4
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: OLCOKGUYNHCXJC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胡椒醛 、 2-氨基苯甲酰胺 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95%的产率得到(S)-2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydroquinazolin-4(1H)-one
  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

• Asymmetric Brønsted Acid Catalysis: Catalytic Enantioselective Synthesis of Highly Biologically Active Dihydroquinazolinones
  作者：Magnus Rueping、Andrey P. Antonchick、Erli Sugiono、Konstantin Grenader

  DOI：10.1002/anie.200804770

  日期：2009.1.19

  Surprisingly straightforward: A metal‐free, highly enantioselective Brønsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3‐dihydroquinazolinones starting from 2‐aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3‐dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than

  出人意料的简单：已开发出一种无金属，高对映选择性的布朗斯台德酸催化的缩合/加成反应，用于从2-氨基苯甲酰胺和醛类化合物（见方案）开始构建2,3-二氢喹唑啉酮。这种有效的方法为2,3-二氢喹唑啉酮提供了对S对映异构体的强烈偏好，S对映异构体比R对映异构体具有更高的生物活性。
• 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.
• 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.