7-nitro-benzo[b]oxepin-3(2H)-one | 497960-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 7-nitro-benzo[b]oxepin-3(2H)-one
• 英文别名: 7-Nitro-1-benzoxepin-3(2H)-one；7-nitro-1-benzoxepin-3-one
• CAS: 497960-74-4
• 化学式: C₁₀H₇NO₄
• 分子量: 205.17
• InChiKey: XHWHSKZVTAFBSU-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  377.3±42.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-硝基水杨醛 、 3-氯-2-氧代三苯基磷酸亚苯酯 在 sodium ethanolate 、 potassium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以34%的产率得到7-nitro-benzo[b]oxepin-3(2H)-one
  参考文献：
  名称：

  Efficient entry to 1-benzoxepine ring skeleton via tandem SN2/Wittig reaction. Total synthesis of NADH: ubiquinone oxidoreductase (complex I) antagonist pterulinic acid

  摘要：

  Concise synthesis of NADH: ubiquinone oxidoreductase (complex I) antagonist pterulinic acid (1a) is reported. The key architectural framework in the natural product, 1-benzoxepine ring skeleton, was smoothly prepared from known salicylaldehyde 2g and phosphorane 3 via tandem S(N)2/Wittig reaction. Pterulinic acid was prepared in 5 steps from 2g with overall yield of 25%. The versatility of tandem S(N)2/Wittig reaction was investigated. This tandem reaction tolerated various alkyl, ether, tertiaryamine and nitro substituted salicylaldehyde, and it gave the corresponding 1-benzoxepine ring skeleton in moderated yield (21-72%). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01658-7

文献信息

• Efficient entry to 1-benzoxepine ring skeleton via tandem SN2/Wittig reaction. Total synthesis of NADH: ubiquinone oxidoreductase (complex I) antagonist pterulinic acid
  作者：Yuh-Lin Lin、Hsien-Shou Kuo、Yi-Wen Wang、Sheng-Tung Huang

  DOI：10.1016/s0040-4020(02)01658-7

  日期：2003.2

  Concise synthesis of NADH: ubiquinone oxidoreductase (complex I) antagonist pterulinic acid (1a) is reported. The key architectural framework in the natural product, 1-benzoxepine ring skeleton, was smoothly prepared from known salicylaldehyde 2g and phosphorane 3 via tandem S(N)2/Wittig reaction. Pterulinic acid was prepared in 5 steps from 2g with overall yield of 25%. The versatility of tandem S(N)2/Wittig reaction was investigated. This tandem reaction tolerated various alkyl, ether, tertiaryamine and nitro substituted salicylaldehyde, and it gave the corresponding 1-benzoxepine ring skeleton in moderated yield (21-72%). (C) 2003 Elsevier Science Ltd. All rights reserved.