methyl (Z)-2-(2-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate

• 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: methyl (Z)-2-(2-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate
• 英文别名: (Z)-methyl 2-(2-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate；methyl (2Z)-2-(2-hydroxy-4H-1,4-benzoxazin-3-ylidene)acetate
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: YSJLLBZUISGYOK-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(Z)-methyl 2-(2-oxo-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate	66628-73-7	C11H9NO4	219.197

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(Z)-methyl 2-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate	——	C25H31NO4	409.525

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-(2-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate 、 间苯二甲醚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到(Z)-methyl 2-(2-(2,4-dimethoxyphenyl)-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate
  参考文献：
  名称：

  BF 3 ·2-乙基-1,4-苯并恶嗪的叶酸介导的Friedel-Crafts芳基化反应：2-芳基-1,4-苯并恶嗪衍生物的合成

  摘要：

  据报道，BF 3 ·醚酸酯介导的2-羟基苯并恶嗪衍生物与各种富电子芳烃的Friedel-Crafts芳基化反应形成了碳-碳键。当前方案为在温和条件下合成一系列密集取代的2-芳基-1,4-苯并恶嗪衍生物提供了便捷途径。

  DOI：

  10.1021/jo402254n
• 作为产物：
  描述：

  (Z)-methyl 2-(2-oxo-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 methyl (Z)-2-(2-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate
  参考文献：
  名称：

  Expedient synthesis of novel 1,4-benzoxazine and butenolide derivatives

  摘要：

  已开发出一种快速高效的合成2-羟基-1,4-苯并噁嗪衍生物的方案。这些中间体作为合成一系列新型丁烯内酯衍生物和2-氨基-1,4-苯并噁嗪衍生物的前体。

  DOI：

  10.1039/c4ra01736f

文献信息

• Expedient synthesis of novel 1,4-benzoxazine and butenolide derivatives
  作者：Garima Choudhary、Ram Tilak Naganaboina、Rama Krishna Peddinti

  DOI：10.1039/c4ra01736f

  日期：——

  A rapid and efficient protocol for the synthesis of 2-hydroxy-1,4-benzoxazine derivatives has been developed. These intermediates served as precursors for the synthesis of a series of novel butenolide derivatives and 2-amino-1,4-benzoxazine derivatives.

  已开发出一种快速高效的合成2-羟基-1,4-苯并噁嗪衍生物的方案。这些中间体作为合成一系列新型丁烯内酯衍生物和2-氨基-1,4-苯并噁嗪衍生物的前体。
• Design, synthesis and antimycobacterial activity of benzoxazinone derivatives and open-ring analogues: Preliminary data and computational analysis
  作者：Daniele Zampieri、Maria Grazia Mamolo、Julia Filingeri、Sara Fortuna、Alessandro De Logu、Adriana Sanna、Davide Zanon

  DOI：10.1016/j.bmcl.2019.07.025

  日期：2019.9

  This study examines in depth benzoxazine nucleus for antimycobacterial property. We synthesized some benzoxazin-2-one and benzoxazin-3-one derivatives, which were tested for activity against a panel of Mycobacterium tuberculosis (Mtb) strains, including H37Ra, H37Rv and some resistant strains. Several compounds displayed a high antimycobacterial activity and the three isoniazid analogue derivatives 8a-c exhibited a MIC range of 0.125-0.250 mu g/mL (0.37-0.75 mu M) against strain H37Ra, therefore lower than the isoniazid reference drug. Two benzoxazin-2-one derivatives, 1c and 5j, together with isoniazid-analogue compound 8a, also revealed low MIC values against resistant strains and proved highly selective for mycobacterial cells, compared to mammalian Vero cells. To predict whether molecule 8a is able to interact with the active site of InhA, we docked it into the crystal structure; indeed, during the molecular dynamic simulation the compound never left the protein pocket. The more active compounds were predicted for ADME properties and all proved to be potentially orally active in humans.
• BF₃·Etherate-Mediated Friedel–Crafts Arylation of 2-Hydroxy-1,4-benzoxazines: Synthesis of 2-Aryl-1,4-benzoxazine Derivatives
  作者：Ram Tilak Naganaboina、Rama Krishna Peddinti

  DOI：10.1021/jo402254n

  日期：2013.12.20

  BF3·etherate-mediated carbon–carbon bond formation by the Friedel–Crafts arylation of 2-hydroxybenzoxazine derivatives with various electron-rich arenes is reported. The current protocol provides an easy access for the synthesis of a series of densely substituted 2-aryl-1,4-benzoxazine derivatives under mild conditions.

  据报道，BF 3 ·醚酸酯介导的2-羟基苯并恶嗪衍生物与各种富电子芳烃的Friedel-Crafts芳基化反应形成了碳-碳键。当前方案为在温和条件下合成一系列密集取代的2-芳基-1,4-苯并恶嗪衍生物提供了便捷途径。