3,4-dihydro-7-methyl-3-phenyl-2H-benzo[b][1,4]oxazine | 324817-87-0

• 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: 3,4-dihydro-7-methyl-3-phenyl-2H-benzo[b][1,4]oxazine
• 英文别名: 3-phenyl-7-methyl-benzomorpholine；7-Methyl-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazine；7-methyl-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine
• CAS: 324817-87-0
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: CSQHIAHUKJDEEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-7-methyl-3-phenyl-2H-benzo[b][1,4]oxazine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 3,7-dihydro-9-methyl-7-oxo-3-phenyl-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
  参考文献：
  名称：

  7-Oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamides as Selective CB₂ Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists

  摘要：

  Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB(2) K-i = 2.5 nM, SI = 166; 21, hCB(2) K-i = 0.81 nM, SI = 383; 38, hCB(2) K-i = 15.8 nM, SI > 633; 56, hCB(2) K-i = 8.12 nM, SI > 1231; (R)-58, hCB(2) K-i = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.

  DOI：

  10.1021/jm300763w
• 作为产物：
  描述：

  7-methyl-3-phenyl-2H-benzo[b][1,4]oxazine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以60%的产率得到3,4-dihydro-7-methyl-3-phenyl-2H-benzo[b][1,4]oxazine
  参考文献：
  名称：

  [EN] LABELED OXAZINOCARBAZOLES AS DIAGNOSTIC AGENTS
  [FR] OXAZINOCARBAZOLES MARQUES UTILES EN TANT QU'AGENTS DE DIAGNOSTIC

  摘要：

  本发明提供了具有环连接位置8（C-8）和位置9（N-9）的同位素标记的噁嗪喹啉衍生物，更具体地提供了符合以下式（I）的化合物，其中R1、R2、R3和R4如本文所述。这些化合物在需要调节5-HT活性的疾病的诊断分析中很有用。

  公开号：

  WO2003089438A1

文献信息

• Ir-Catalyzed Enantioselective Hydrogenation of 2<i>H</i>-1,4-Benzoxazines with a Chiral 1,2,3,4-Tetrahydro-1-naphthylamine Derived Phosphine-aminophosphine Ligand
  作者：Juan Hu、Daoyong Wang、Zhuo Zheng、Xiangping Hu

  DOI：10.1002/cjoc.201200944

  日期：2012.11

  Unsymmetrical hybrid chiral phosphine‐aminophosphine ligand derived from 1,2,3,4‐tetrahydro‐1‐naphthylamine has been found to be highly efficient in the Ir‐catalyzed asymmetric hydrogenation of various 3‐aryl‐2H‐1,4‐benzoxazines, providing good enantioselectivities (up to 95% ee) and high catalytic activity (S/C up to 5000).

  已发现衍生自1,2,3,4-四氢-1-萘胺的不对称杂化手性膦-氨基膦配体在各种3-芳基-2 H -1,4-苯并恶嗪的Ir催化不对称氢化中非常有效，提供良好的对映选择性（高达95％ee）和高催化活性（S / C高达5000）。
• US4288589A
  申请人：——

  公开号：US4288589A

  公开（公告）日：1981-09-08