4-((2-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)methyl)benzonitrile | 1034767-25-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-((2-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)methyl)benzonitrile
• 英文别名: 4-[(2-oxo-3H-1,4-benzoxazin-4-yl)methyl]benzonitrile
• CAS: 1034767-25-3
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: XFAPRFNJPCGFAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((2-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)methyl)benzonitrile 、 偶氮二甲酸二异丙酯 以 乙腈 为溶剂， 以55%的产率得到diisopropyl 1-(4-(4-cyanobenzyl)-2-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  在无金属和光催化剂条件下，用偶氮二羧酸二烷基酯对喹喔啉-2-酮和苯并[1,4]恶嗪-2-酮进行可见光加速胺化

  摘要：

  描述了在金属和无光催化剂条件下通过可见光照射加速的环胺（二氢喹喔啉酮和二氢苯并恶嗪酮）与偶氮二羧酸二烷基酯的直接 sp 3 C-H 胺化。该协议具有非常温和的反应条件，用于合成氨基喹喔啉和苯并恶嗪衍生物，产率从好到高（高达 99%）。这些缩醛胺衍生物代表了用于不同合成 quinoxalin-2-one 衍生物的通用构件。

  DOI：

  10.1039/d1ob01157j
• 作为产物：
  描述：

  ethyl (2-hydroxyphenyl)glycinate 、 4-氰基苯甲醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到4-((2-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)methyl)benzonitrile
  参考文献：
  名称：

  A convenient synthesis of 3,4-dihydro-1,4-benzoxazin-2-ones

  摘要：

  3,4-Dihydro-1,4-benzoxazin-2-one was prepared for the first time by catalytic hydrogenation of 4-benzyl-3,4-dihydro-1,4-benzoxazin-2-one. A simple and efficient synthesis of 4-benzyl- and 4-alkyl-3,4-dihydro-1,4-benzoxazin-2-one derivatives from ethyl 2-(2-hydroxyphenylamino)acetate and aldehydes is described. Some considerations regarding the reactivity of 3,4-dihydro-1,4-benzoxazin-2-ones are given. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.010

文献信息

• A Metallaphotoredox Method for the Expansion of Benzyl SAR on Electron-Deficient Amines
  作者：Meghan D. Shea、Umar Faruk Mansoor、Brett A. Hopkins

  DOI：10.1021/acs.orglett.9b04587

  日期：2020.2.7

  A metallaphotoredox reaction is described that allows for the efficient exploration of benzyl structure-activity relationships on electron-deficient amines. Typically, accessing a variety of benzyl groups on these substrates can be difficult due to the limited availability of the prerequisite building blocks, namely benzyl halides. However, the use of aryl bromides in this metallaphotoredox reaction allows for greater diversity in the benzyl piece. The reaction scope is discussed herein, including conditions for product scaleup using flow.
• Visible-light-accelerated amination of quinoxalin-2-ones and benzo[1,4]oxazin-2-ones with dialkyl azodicarboxylates under metal and photocatalyst-free conditions
  作者：Jaume Rostoll-Berenguer、Murta Capella-Argente、Gonzalo Blay、José R. Pedro、Carlos Vila

  DOI：10.1039/d1ob01157j

  日期：——

  A direct sp3 C–H amination of cyclic amines (dihydroquinoxalinones and dihydrobenzoxazinones) with dialkyl azo dicarboxylates accelerated by visible-light irradiation under metal and photocatalyst-free conditions is described. This protocol features very mild reaction conditions for the synthesis of aminal quinoxaline and benzoxazine derivatives with good to high yields (up to 99%). These aminal derivatives

  描述了在金属和无光催化剂条件下通过可见光照射加速的环胺（二氢喹喔啉酮和二氢苯并恶嗪酮）与偶氮二羧酸二烷基酯的直接 sp 3 C-H 胺化。该协议具有非常温和的反应条件，用于合成氨基喹喔啉和苯并恶嗪衍生物，产率从好到高（高达 99%）。这些缩醛胺衍生物代表了用于不同合成 quinoxalin-2-one 衍生物的通用构件。
• A convenient synthesis of 3,4-dihydro-1,4-benzoxazin-2-ones
  作者：Nace Zidar、Danijel Kikelj

  DOI：10.1016/j.tet.2008.04.010

  日期：2008.6

  3,4-Dihydro-1,4-benzoxazin-2-one was prepared for the first time by catalytic hydrogenation of 4-benzyl-3,4-dihydro-1,4-benzoxazin-2-one. A simple and efficient synthesis of 4-benzyl- and 4-alkyl-3,4-dihydro-1,4-benzoxazin-2-one derivatives from ethyl 2-(2-hydroxyphenylamino)acetate and aldehydes is described. Some considerations regarding the reactivity of 3,4-dihydro-1,4-benzoxazin-2-ones are given. (C) 2008 Elsevier Ltd. All rights reserved.