(RS)-5-benzoyl-3,3-bis(hydroxymethyl)-8a-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-8(8aH)-one | 167566-26-9

• 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: (RS)-5-benzoyl-3,3-bis(hydroxymethyl)-8a-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-8(8aH)-one
• 英文别名: 5-Benzoyl-8a-hydroxy-3,3-bis(hydroxymethyl)-2,4-dihydro-1,4-benzoxazin-8-one
• CAS: 167566-26-9
• 化学式: C₁₇H₁₇NO₆
• 分子量: 331.325
• InChiKey: FWTAQXCQZPKZDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (RS)-5-benzoyl-3,3-bis(hydroxymethyl)-8a-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-8(8aH)-one 以 甲醇 为溶剂， 反应 0.5h， 生成 (8-Benzylamino-3,3-bis-hydroxymethyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-yl)-phenyl-methanone
  参考文献：
  名称：

  A convenient two-step one-pot electrochemical synthesis of novel 8-amino-1,4-benzoxazine derivatives possessing anti-stress oxidative properties

  摘要：

  Using (3,4-hydroxy-2-methoxyphenyl) (phenyl) methanone as the starting material, the reaction of the electrogenerated 3,4-quinone with amino alcohols leads to the transient 1,4-benzoxazin-8-one species. The latter can undergo a subsequent addition reaction of an amine at the 8-position affording, after electrochemical reduction, novel 8-amino-1,4-benzoxazine derivatives. The entire sequence can be conducted in one-pot, without isolation of intermediates. (C),1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02037-1
• 作为产物：
  描述：

  三羟甲基氨基甲烷 、 (3,4-dihydroxy-2-methoxyphenyl) (phenyl) methanone 以 甲醇 为溶剂， 以66%的产率得到(RS)-5-benzoyl-3,3-bis(hydroxymethyl)-8a-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-8(8aH)-one
  参考文献：
  名称：

  Largeron, Martine; Langevin-Bermond, Dominique; Fleury, Maurice-Bernard, Journal of the Chemical Society. Perkin transactions II, 1996, # 5, p. 893 - 900

  摘要：

  DOI：

文献信息

• Novel 1,4-benzoxazine derivatives of pharmacological interest. Electrochemical and chemical syntheses
  作者：Martine Largeron、Hélène Dupuy、Maurice-Bernard Fleury

  DOI：10.1016/0040-4020(95)98693-c

  日期：1995.4

  The reaction of electrochemically or chemically generated orthoquinones with aminoalcohols, in methanol, affords a convenient route to novel 1,4-benzoxazine derivatives. Some of these compounds are found to possess interesting pharmacological properties.

  在甲醇中，电化学或化学生成的邻苯二酚与氨基醇的反应为新型1,4-苯并恶嗪衍生物的合成提供了便利的途径。发现这些化合物中的一些具有令人感兴趣的药理性质。
• Synthesis and in Vitro Evaluation of New 8-Amino-1,4-benzoxazine Derivatives as Neuroprotective Antioxidants
  作者：Martine Largeron、Brian Lockhart、Bruno Pfeiffer、Maurice-Bernard Fleury

  DOI：10.1021/jm991105j

  日期：1999.12.2

  A series of new 8-amino-1,4-benzoxazine derivatives 5a-o was synthesized and examined for their intrinsic cytotoxicity and their capacity to inhibit oxidative stress-mediated neuronal degeneration in neuronal cell cultures. In particular, substituent effects at the 3- and 8-positions of the 1,4-benzoxazine ring were investigated by in vitro evaluation.. In this aim, 3-alkyl substituents seemed to be essential for efficient neuroprotective activity. Furthermore, within the subseries of substituted S-alkyl benzoxazines, the most active derivatives were those bearing an 8-benzylamino substituent. From the combined results of both toxicity and neuroprotection expressed in terms of the safety index, 8-benzylamino-substituted-3-alkyl-1,4-benzoxazines were identified as the most promising compounds, owing to their potent neuroprotective activity without the manifestation of intrinsic cytotoxicity.