5-nitrospiro<1,3-benzodioxole-2,1'-cyclohexane> | 64179-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-nitrospiro<1,3-benzodioxole-2,1'-cyclohexane>
• 英文别名: 4-nitrocatechol cyclohexylidene ketal；5-Nitrospiro[1,3-benzodioxole-2,1'-cyclohexane]
• CAS: 64179-40-4
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD01463454
• 分子量: 235.24
• InChiKey: DGGQZKWSSUCGHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitrospiro<1,3-benzodioxole-2,1'-cyclohexane> 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 螺[1,3-苯并二氧戊环-2,1'-环己烷]-5-胺
  参考文献：
  名称：

  Comparative toxicities and analgesic activities of three monomethylated analogs of acetaminophen

  摘要：

  Three monomethylated derivatives of 4'-hydroxyacetanilide (acetaminophen) were prepared in order to compare their cytotoxic potential and analgesic activity with that of acetaminophen. Only 4'-hydroxy-N-methylacetanilide (N-methylacetaminophen) was devoid of cytotoxic effects to hepatic tissue of mice. Results of comparative tissue distribution studies and metabolism studies both in vivo and in vitro in mice indicate that the disposition of N-methylacetaminophen is similar to that of acetaminophen except that it is not oxidized to a toxic metabolite. In contrast, 3'-methyl-4'-hydroxyacetanilide (3-methylacetaminophen) is as hepatotoxic as acetaminophen in mice while 2'-methyl-4'-hydroxyacetanilide (2-methylacetaminophen) is less hepatotoxic. The analgesic potency of the analogues seems to parallel their hepatotoxic potential, and both activities parallel the oxidation potentials in this series of compounds.

  DOI：

  10.1021/jm00159a029
• 作为产物：
  描述：

  环己酮缩邻苯二酚 在 硝酸 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以80.7%的产率得到5-nitrospiro<1,3-benzodioxole-2,1'-cyclohexane>
  参考文献：
  名称：

  Comparative toxicities and analgesic activities of three monomethylated analogs of acetaminophen

  摘要：

  Three monomethylated derivatives of 4'-hydroxyacetanilide (acetaminophen) were prepared in order to compare their cytotoxic potential and analgesic activity with that of acetaminophen. Only 4'-hydroxy-N-methylacetanilide (N-methylacetaminophen) was devoid of cytotoxic effects to hepatic tissue of mice. Results of comparative tissue distribution studies and metabolism studies both in vivo and in vitro in mice indicate that the disposition of N-methylacetaminophen is similar to that of acetaminophen except that it is not oxidized to a toxic metabolite. In contrast, 3'-methyl-4'-hydroxyacetanilide (3-methylacetaminophen) is as hepatotoxic as acetaminophen in mice while 2'-methyl-4'-hydroxyacetanilide (2-methylacetaminophen) is less hepatotoxic. The analgesic potency of the analogues seems to parallel their hepatotoxic potential, and both activities parallel the oxidation potentials in this series of compounds.

  DOI：

  10.1021/jm00159a029

文献信息

• WO2007/10085
  申请人：——

  公开号：——

  公开（公告）日：——
• HARVISON P. J.; FORTE A. J.; NELSON S. D., J. MED. CHEM., 29,(1986) N 9, 1737-1743
  作者：HARVISON P. J.、 FORTE A. J.、 NELSON S. D.

  DOI：——

  日期：——
• CLARK R. L.; PESSOLANO A. A.; SHEN T.-Y.; JACOBUS D. P.; JONES H.; LOTTI +, J. MED. CHEM., 1978, 21, NO 9, 965-978
  作者：CLARK R. L.、 PESSOLANO A. A.、 SHEN T.-Y.、 JACOBUS D. P.、 JONES H.、 LOTTI +

  DOI：——

  日期：——
• Comparative toxicities and analgesic activities of three monomethylated analogs of acetaminophen
  作者：Peter J. Harvison、Anthony J. Forte、Sidney D. Nelson

  DOI：10.1021/jm00159a029

  日期：1986.9

  Three monomethylated derivatives of 4'-hydroxyacetanilide (acetaminophen) were prepared in order to compare their cytotoxic potential and analgesic activity with that of acetaminophen. Only 4'-hydroxy-N-methylacetanilide (N-methylacetaminophen) was devoid of cytotoxic effects to hepatic tissue of mice. Results of comparative tissue distribution studies and metabolism studies both in vivo and in vitro in mice indicate that the disposition of N-methylacetaminophen is similar to that of acetaminophen except that it is not oxidized to a toxic metabolite. In contrast, 3'-methyl-4'-hydroxyacetanilide (3-methylacetaminophen) is as hepatotoxic as acetaminophen in mice while 2'-methyl-4'-hydroxyacetanilide (2-methylacetaminophen) is less hepatotoxic. The analgesic potency of the analogues seems to parallel their hepatotoxic potential, and both activities parallel the oxidation potentials in this series of compounds.