3-benzyl-6-chloro-2-phenylquinazolin-4(3H)-one | 7012-92-2

• 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: 3-benzyl-6-chloro-2-phenylquinazolin-4(3H)-one
• 英文别名: 3-Benzyl-6-chloro-2-phenylquinazolin-4-one；3-benzyl-6-chloro-2-phenylquinazolin-4-one
• CAS: 7012-92-2
• 化学式: C₂₁H₁₅ClN₂O
• 分子量: 346.816
• InChiKey: BTFCKNVZJSOSJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 3-benzyl-6-chloro-2-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  One pot synthesis of some new N-allyl and N-benzyl quinazolinones and their anti-inflammatory activity

  摘要：

  DOI：

  10.1016/j.jics.2021.100033

文献信息

• Tandem Oxidative Cyclocondensation towards 2,3-Disubstituted Quinazolinones in the Presence of [Bmim][BF₄ ] and Iodine
  作者：Firdoos Ahmad Sofi、Rohit Sharma、Asit K. Chakraborti、Prasad V. Bharatam

  DOI：10.1002/ejoc.201900969

  日期：2019.9.15

  Metal‐free access to 2,3‐disubstituted quinazolinones following a tandem oxidative cyclo‐condensation of istoic anhydrides with arylmethylamines mediated by [Bmim][BF4] and Iodine is reported. The arylmethylamines serve as the common precursor for the C‐2 and N‐3 substituents.

  据报道，在[Bmim] [BF4]和碘介导的条件下，对等酸酐与芳基甲胺进行串联氧化环缩合后，无金属地获得2,3-二取代的喹唑啉酮。芳基甲胺是C-2和N-3取代基的常见前体。
• Copper-catalyzed redox-neutral C–H amination with amidoximes
  作者：Hui Chen、Shunsuke Chiba

  DOI：10.1039/c3ob41871e

  日期：——

  CuI-catalyzed reactions of N-alkylamidoximes afforded dihydroimidazoles via sp3 C–H amination. On the other hand, the reactions of N-benzoylamidoximes resulted in sp2 C–H amination to form quinazolinones. The reaction mechanisms could be characterized as a redox-neutral radical pathway including a Cu(I)–Cu(II) redox catalytic cycle.

  CuI催化的N-烷基氨基肟反应通过sp³ C–H氨化生成了二氢咪唑。另一方面，N-苯甲酰氨基肟的反应产生了sp² C–H氨化，形成奎嗪酮。反应机制可以被描述为一种红氧中性自由基途径，包括Cu(I)–Cu(II)的红氧催化循环。
• Rhodium(II)-Catalyzed Carbenoid Insertion of<i>N</i>-Tosylhydrazones into Amide NH Bonds: An Efficient Approach to<i>N</i>³-Benzyl/Alkyl-2-arylquinazolinones
  作者：Rajaka Lingayya、Mari Vellakkaran、Kommu Nagaiah、Jagadeesh Babu Nanubolu

  DOI：10.1002/adsc.201500678

  日期：2016.1.7

  Dirhodium(II) acetate‐catalyzed reactions of N‐tosylhydrazones with dihydroquinazolinones bearing different types of NH bonds that give N3‐benzyl/alkyl‐2‐arylquinazolin‐4(3H)‐ones through Csp3N bond formation by oxidative dehydrogenation and insertion of rhodium‐carbenoid into amide NH bond are reported for the first time. This method features good to excellent yields, good functional group tolerance

  二铑（II），乙酸催化的反应Ñ与dihydroquinazolinones轴承不同类型的N个-tosylhydrazones  H键，给Ñ 3 -苄基/烷基-2- arylquinazolin-4（3 ħ） -酮至C SP 3  N键形成通过氧化脱氢和铑卡宾插入酰胺ñ  H键报道首次。该方法具有良好至优异的产率，良好的官能团耐受性，高区域选择性和易于获得的起始原料的特征。
• Ligand-Free Pd-Catalyzed and Copper-Assisted C–H Arylation of Quinazolin-4-ones with Aryl Iodides under Microwave Heating
  作者：Sylvain Laclef、Marine Harari、Julien Godeau、Isabelle Schmitz-Afonso、Laurent Bischoff、Christophe Hoarau、Vincent Levacher、Corinne Fruit、Thierry Besson

  DOI：10.1021/acs.orglett.5b00467

  日期：2015.4.3

  A microwave-assisted method for the palladium-catalyzed direct arylation of quinazolin-4-one has been developed under copper-assistance. This method is applicable to a wide range of aryl iodides and substituted (2H)-quinazolin-4-ones. This protocol provides a simple and efficient way to synthesize biologically relevant 2-arylquinazolin-4-one backbones.
• One pot synthesis of some new N-allyl and N-benzyl quinazolinones and their anti-inflammatory activity
  作者：Sudharshan Reddy Sudula、Ranjith Jala、Kavitha Siddoju、Jagadeesh Kumar Ega

  DOI：10.1016/j.jics.2021.100033

  日期：2021.3