2,2-Dimethylspiro[3,4-dihydrobenzo[h]chromene-6,2'-oxirane]-5-one | 64184-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2,2-Dimethylspiro[3,4-dihydrobenzo[h]chromene-6,2'-oxirane]-5-one
• CAS: 64184-03-8
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: SJZYPEHDIVSSAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Dimethylspiro[3,4-dihydrobenzo[h]chromene-6,2'-oxirane]-5-one 在 碘 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以87%的产率得到
  参考文献：
  名称：

  用β-拉帕酮合成新的羰基和氟代烷基邻醌甲基化物

  摘要：

  据报道由β-拉帕酮合成新的羰基和氟代烷基邻醌甲基化物。

  DOI：

  10.1016/j.tetlet.2007.06.145
• 作为产物：
  描述：

  重氮甲烷 、 3,4-二氢-2,2-二甲基-2H-萘并[1,2-B]吡喃-5,6-二酮 以 乙醚 为溶剂， 以94%的产率得到2,2-Dimethylspiro[3,4-dihydrobenzo[h]chromene-6,2'-oxirane]-5-one
  参考文献：
  名称：

  用β-拉帕酮合成新的羰基和氟代烷基邻醌甲基化物

  摘要：

  据报道由β-拉帕酮合成新的羰基和氟代烷基邻醌甲基化物。

  DOI：

  10.1016/j.tetlet.2007.06.145

文献信息

• Trypanocidal agents with low cytotoxicity to mammalian cell line: A comparison of the theoretical and biological features of lapachone derivatives
  作者：Vitor F. Ferreira、Alessandra Jorqueira、Alessandra M.T. Souza、Milton N. da Silva、Maria C.B.V. de Souza、Robson M. Gouvêa、Carlos R. Rodrigues、Antonio V. Pinto、Helena C. Castro、Dilvani O. Santos、Humberto P. Araújo、Saulo C. Bourguignon

  DOI：10.1016/j.bmc.2006.04.046

  日期：2006.8

  Starting from alpha- and beta-lapachones, in this work we compared the biological and theoretical profile of several oxyran derivatives of lapachone as potential trypanocidal agents. Our biological results showed that the oxyrans tested act as trypanocidal agents against Trypanosoma cruzi with minimal cytotoxicity in the VERO cell line compared to naphthoquinones. The oxyran derivative of alpha-lapachone (7a) showed to be one of the most potent compounds. In our molecular modeling study, we analyzed the C-ring moiety and the redox center of beta-lapachone molecule as the moieties responsible for the trypanocidal and cytotoxic effects on mammalian cell line. The computational methods used to delineate the structural requirements for the trypanocidal profile pointed out that the transposition of the C-ring moiety of beta-lapachone, combined with its oxyran ring, introduced important molecular requirements for trypanocidal activity in the HOMO energy, HOMO orbital coefficient, LUMO density, electrostatic potential map, dipole moment vector, and calculated logP (c logP) parameter. This study could lead to the development of new antichagasic medicines based on alpha-lapachone analogs. (c) D2006 Elsevier Ltd. All rights reserved.
• Synthesis of new carbonyl and fluoroalkyl o-quinone methides from β-lapachone
  作者：Milton N. da Silva、Sabrina B. Ferreira、Alessandra Jorqueira、Maria C.B.V. de Souza、Antonio V. Pinto、Carlos R. Kaiser、Vitor F. Ferreira

  DOI：10.1016/j.tetlet.2007.06.145

  日期：2007.8

  The synthesis of new carbonyl and fluoroalkyl o-quinone methides from β-lapachone is reported.

  据报道由β-拉帕酮合成新的羰基和氟代烷基邻醌甲基化物。