3-(2-benzyloxyethyl)-3,7-methyl-1,2-dioxaspiro[4.5]decane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-benzyloxyethyl)-3,7-methyl-1,2-dioxaspiro[4.5]decane
• 英文别名: 3,7-Dimethyl-3-(2-phenylmethoxyethyl)-1,2-dioxaspiro[4.5]decane
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: IDCKVARGJWZJOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基环己酮 在 4-二甲氨基吡啶 、 双氧水 、 四氯化锡 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 3-(2-benzyloxyethyl)-3,7-methyl-1,2-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Synthesis of 1,2-Dioxolanes by Annulation Reactions of Peroxycarbenium Ions with Alkenes

  摘要：

  The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized in three steps from the corresponding ketone and alkene.

  DOI：

  10.1021/ol051703u

文献信息

• Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum
  作者：Derek C. Martyn、Armando P. Ramirez、Meaghan J. Beattie、Joseph F. Cortese、Vishal Patel、Margaret A. Rush、K.A. Woerpel、Jon Clardy

  DOI：10.1016/j.bmcl.2008.10.083

  日期：2008.12

  Artemisinin-derived compounds play an integral role in current malaria chemotherapy. Given the virtual certainty of emerging resistance, we have investigated spiro-1,2-dioxolanes as an alternative scaffold. The endoperoxide functionality was generated by the SnCl(4)-mediated annulation of a bis-silylperoxide and an alkene. The first set of eight analogs gave EC(50) values of 50-150 nM against Plasmodium falciparum 3D7 and Dd2 strains, except for the carboxylic acid analog. A second series, synthesized by coupling a spiro-1,2-dioxolane carboxylic acid to four separate amines, afforded the most potent compound ( EC50 similar to 5 nM). (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 1,2-Dioxolanes by Annulation Reactions of Peroxycarbenium Ions with Alkenes
  作者：Armando Ramirez、K. A. Woerpel

  DOI：10.1021/ol051703u

  日期：2005.10.1

  The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized in three steps from the corresponding ketone and alkene.