6-methyl-8-bromo-1,4-benzoxazin-3(2H)-one | 108959-12-2

• 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: 6-methyl-8-bromo-1,4-benzoxazin-3(2H)-one
• 英文别名: 8-bromo-6-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one；8-bromo-6-methyl-4H-1,4-benzoxazin-3-one
• CAS: 108959-12-2
• 化学式: C₉H₈BrNO₂
• 分子量: 242.072
• InChiKey: FMOZIFYYHSGUMU-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solv: ethanol (64-17-5))
• 沸点：
  384.1±42.0 °C(Predicted)
• 密度：
  1.589±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-8-bromo-1,4-benzoxazin-3(2H)-one 在 tris(dibenzylideneacetone)dipalladium (0) 吡啶 、 dimethyl sulfide borane 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 tert-butyl 4-(4-((2-fluorophenyl)sulfonyl)-6-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  3,4-Dihydro-2H-benzo[1,4]oxazine derivatives as 5-HT6 receptor antagonists

  摘要：

  A series of novel 3,4-dihydro-2H-benzo[1,4]oxazine derivatives has been designed and synthesized as 5-HT6 receptor antagonists. Many of the compounds displayed subnanomolar affinities for the 5-HT6 receptor and good brain penetration in rats. The relationship of structure and lipophilicity to hERG inhibition of this series of compounds is discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.093
• 作为产物：
  描述：

  2-溴-4-甲基-6-硝基苯酚 在 sodium dithionite 、 sodium carbonate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 10.0h， 生成 6-methyl-8-bromo-1,4-benzoxazin-3(2H)-one
  参考文献：
  名称：

  3,4-Dihydro-2H-benzo[1,4]oxazine derivatives as 5-HT6 receptor antagonists

  摘要：

  A series of novel 3,4-dihydro-2H-benzo[1,4]oxazine derivatives has been designed and synthesized as 5-HT6 receptor antagonists. Many of the compounds displayed subnanomolar affinities for the 5-HT6 receptor and good brain penetration in rats. The relationship of structure and lipophilicity to hERG inhibition of this series of compounds is discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.093

文献信息

• Hogale; Mulik; Nikam, Journal of the Indian Chemical Society, 1990, vol. 67, # 11, p. 923 - 925
  作者：Hogale、Mulik、Nikam

  DOI：——

  日期：——
• Hogale, M. B.; Dhore, N. P.; Khot, B. R., Journal of the Indian Chemical Society, 1986, vol. 63, p. 412 - 413
  作者：Hogale, M. B.、Dhore, N. P.、Khot, B. R.

  DOI：——

  日期：——
• HOGALE, M. B.;MULIK, A. R.;NIKAM, B. P., J. INDIAN CHEM. SOC., 67,(1990) N1, C. 923-924
  作者：HOGALE, M. B.、MULIK, A. R.、NIKAM, B. P.

  DOI：——

  日期：——
• HOGALE M. B.; DHORE N. P.; KHOT B. R., J. INDIAN CHEM. SOC., 63,(1986) N 4, 412-413
  作者：HOGALE M. B.、 DHORE N. P.、 KHOT B. R.

  DOI：——

  日期：——
• 3,4-Dihydro-2H-benzo[1,4]oxazine derivatives as 5-HT6 receptor antagonists
  作者：Shu-Hai Zhao、Jacob Berger、Robin D. Clark、Steven G. Sethofer、Nancy E. Krauss、Julie M. Brothers、Renee S. Martin、Dinah L. Misner、Dietmar Schwab、Ludmila Alexandrova

  DOI：10.1016/j.bmcl.2006.12.093

  日期：2007.6

  A series of novel 3,4-dihydro-2H-benzo[1,4]oxazine derivatives has been designed and synthesized as 5-HT6 receptor antagonists. Many of the compounds displayed subnanomolar affinities for the 5-HT6 receptor and good brain penetration in rats. The relationship of structure and lipophilicity to hERG inhibition of this series of compounds is discussed. (c) 2007 Elsevier Ltd. All rights reserved.