2-(2-bromophenyl)-5-chloro-4H-benzo[d][1,3]oxazin-4-one | 1234707-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(2-bromophenyl)-5-chloro-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 5-chloro-2-(2-bromophenyl)-4H-benzo[d][1,3]oxazin-4-one；2-(2-bromophenyl)-5-chloro-4H-3,1-benzoxazin-4-one；2-(2-bromophenyl)-5-chloro-3,1-benzoxazin-4-one
• CAS: 1234707-32-4
• 化学式: C₁₄H₇BrClNO₂
• 分子量: 336.572
• InChiKey: WXWVDINGZQKMMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴苯甲酰氯 在 叔丁基过氧化氢 、 [(1,2,3,4,5-pentamethylcyclopentadienyl)*Co(CH₃CN)₃](SbF₆)₂ 、 盐酸羟胺 、 potassium carbonate 、 对氯苯胺 、 cobalt(II) chloride 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 17.0h， 生成 2-(2-bromophenyl)-5-chloro-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  使用瞬态导向基团钴催化苯甲醛与重氮恶唑酮的邻位C（sp2）–H酰胺化

  摘要：

  利用二恶唑酮作为胺化试剂，开发了一种高效便捷的钴催化的苯甲醛邻位-C（sp 2）-H酰胺化反应。该方案的关键特征是使用绿色和经济的地球上富裕的金属钴作为催化剂，对氯苯胺作为瞬态导向基团。通过合成C1r丝氨酸蛋白酶抑制剂45和弹性蛋白酶抑制剂49证明了我们方法的进一步应用。

  DOI：

  10.1021/acs.orglett.9b02632

文献信息

• <i>o</i>-Acetoxylation of oxo-benzoxazines <i>via</i> C–H activation by palladium(<scp>ii</scp>)/aluminium oxide
  作者：Ramanand Prajapati、Ajay Kant Gola、Amrendra Kumar、Shubham Jaiswal、Narender Tadigoppula

  DOI：10.1039/d2nj00134a

  日期：——

  Direct activation of sp2 C–H bonds by a palladium catalyst has received significant attention in organic chemistry. However, most of these C–H activation reactions are carried out in hazardous solvents. Herein we report a novel solvent-free direct sp2 C–H bond functionalization (oxygenation) method using Pd(II)/Al2O3 catalysis of oxo-benzoxazine derivatives with good to excellent yields, and demonstrate

  钯催化剂直接活化sp 2 C-H键在有机化学中受到了广泛关注。然而，大多数这些 C-H 活化反应是在危险溶剂中进行的。在此，我们报道了一种使用 Pd( II )/Al 2 O 3催化氧代苯并恶嗪衍生物的新型无溶剂直接 sp 2 C-H 键官能化（氧化）方法，并证明了其在合成药学上重要的化合物。
• BENZOXAZINONE COMPOUND, METHOD FOR PRODUCING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  申请人：Hsieh Pei-Wen

  公开号：US20110319611A1

  公开（公告）日：2011-12-29

  A benzoxazinone compound having the following formula (I): wherein one of R 1 and R 2 is H, and the other of R 1 and R 2 is a halogen group, and R 1 and R 2 cannot be the same at the same time; and R 3 , R 4 , R 5 , R 6 , and R 7 are independently selected from the group consisting of H, a halogen group, a C 1 -C 4 alkyl group, and a C 1 -C 4 alkoxyl group.

  具有以下式子(I)的苯并噁唑酮化合物：其中R1和R2中的一个是H，另一个是卤素基团，且R1和R2不能同时相同；R3、R4、R5、R6和R7分别独立地选自H、卤素基团、C1-C4烷基和C1-C4烷氧基组成的群。
• Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats
  作者：Pei-Wen Hsieh、Huang-Ping Yu、Yi-Ju Chang、Tsong-Long Hwang

  DOI：10.1016/j.ejmech.2010.03.046

  日期：2010.7

  A new series of benzoxazinone analogs were designed, synthesized, and assayed to determine their effects on superoxide anion generation and neutrophil elastase (NE) release in formyl-L-methionyl-L-leucyl-L-phenylalanine (FMLP)-activated human neutrophils. Of these, compounds 6-10 showed a potent dual inhibitory effect on NE release and superoxide anion generation. In contrast, compounds 11-15 exhibited highly selective and potent inhibitory activities on NE release. These results indicate that the inhibitory activity on NE release in FMLP-activated human neutrophils depended on the position of chloro-substituent in the A ring. On the other hand, 13 significantly attenuated the increase in myeloperoxidase (MPO) activity and edema in the lung of rats after trauma-hemorrhagic shock. Therefore, these compounds could be developed as new NE inhibitors. (c) 2010 Elsevier Masson SAS. All rights reserved.
• Cobalt-Catalyzed <i>Ortho</i>-C(sp²)–H Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Groups
  作者：Jie Huang、Jun Ding、Tong-Mei Ding、Shuiyi Zhang、Yaqiu Wang、Feng Sha、Shu-Yu Zhang、Xin-Yan Wu、Qiong Li

  DOI：10.1021/acs.orglett.9b02632

  日期：2019.9.20

  An efficient and convenient cobalt-catalyzed ortho-C(sp2)–H amidation of benzaldehydes employing dioxazolones as the aminating reagent has been developed. The key feature of this protocol is the use of green and economic earth-abundant metals cobalt as the catalyst with the p-chloroaniline as the transient directing group. Further application of our approach was demonstrated by the synthesis of C1r

  利用二恶唑酮作为胺化试剂，开发了一种高效便捷的钴催化的苯甲醛邻位-C（sp 2）-H酰胺化反应。该方案的关键特征是使用绿色和经济的地球上富裕的金属钴作为催化剂，对氯苯胺作为瞬态导向基团。通过合成C1r丝氨酸蛋白酶抑制剂45和弹性蛋白酶抑制剂49证明了我们方法的进一步应用。