8-hydroxy-7-iodo-benzo[b]oxepin-3(2H)-one | 530087-09-3

• 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: 8-hydroxy-7-iodo-benzo[b]oxepin-3(2H)-one
• 英文别名: 8-Hydroxy-7-iodo-1-benzoxepin-3-one
• CAS: 530087-09-3
• 化学式: C₁₀H₇IO₃
• 分子量: 302.068
• InChiKey: CCYSGMQXCRCBJP-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  361.2±42.0 °C(Predicted)
• 密度：
  1.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-7-iodo-benzo[b]oxepin-3(2H)-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 methyl (7-chloromethylene-7,8-dihydro-1,9-dioxa-cyclohepta[f]inden-2-yl)acetate
  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
• 作为产物：
  描述：

  7-iodo-8-methoxymethoxy-benzo[b]oxepin-3(2H)-one 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以99%的产率得到8-hydroxy-7-iodo-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