2-(2'-acetylphenylamino)-5-(ethylthio)benzo[1,4]quinone | 244241-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2'-acetylphenylamino)-5-(ethylthio)benzo[1,4]quinone
• 英文别名: 2-(2-Acetylanilino)-5-ethylsulfanylcyclohexa-2,5-diene-1,4-dione
• CAS: 244241-78-9
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: DEIPKSSUKJYKEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2'-acetylphenylamino)-5-(ethylthio)benzo[1,4]quinone 在 硫酸 、 溶剂黄146 作用下， 反应 0.08h， 以81%的产率得到2-ethylthio-9-methyl-acridine[1,4]dione
  参考文献：
  名称：

  A Convenient New Route to 4-Substituted Benzo[de][3,6]Phenanthrolin-6(6H)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin

  摘要：

  4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.

  DOI：

  10.1080/00397919908086428
• 作为产物：
  描述：

  2-(ethylthio)benzo[1,4]quinone 、 邻氨基苯乙酮 在 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 192.0h， 以48%的产率得到2-(2'-acetylphenylamino)-5-(ethylthio)benzo[1,4]quinone
  参考文献：
  名称：

  A Convenient New Route to 4-Substituted Benzo[de][3,6]Phenanthrolin-6(6H)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin

  摘要：

  4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.

  DOI：

  10.1080/00397919908086428

文献信息

• A Convenient New Route to 4-Substituted Benzo[<i>de</i>][3,6]Phenanthrolin-6(6<i>H</i>)-Ones: Important Intermediates in the Synthesis of Ring-A Analogues of the Cytotoxic Marine Alkaloid Ascididemin
  作者：Brent R. Copp、Richard P. Hansen、David R. Appleton、Brent S. Lindsay、Chris J. Squire、George R. Clark、Cliff E. F. Rickard

  DOI：10.1080/00397919908086428

  日期：1999.8.1

  4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.