2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetic acid | 1101829-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetic acid
• CAS: 1101829-37-1
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: RYYOUCAVNXZGPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苄胺 、 2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以56%的产率得到2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)-N-(3,4,5-trimethoxybenzyl)acetamide
  参考文献：
  名称：

  Synthesis and in vitro DMPK profiling of a 1,2-dioxolane-based library with activity against Plasmodium falciparum

  摘要：

  A 43-member 1,2-dioxolane library was synthesized by coupling a 1,2-dioxolane-3-acetic acid derivative to a range of amines. Ten compounds had EC(50)s <= 30 nM against Plasmodium falciparum 3D7 and Dd2 strains, and another 15 compounds had EC(50)s <= 50 nM against both 3D7 and Dd2. The library was then subjected to a range of in vitro DMPK assays, which revealed that side chains with a heteroatom were required for favorable solubility, Log D and membrane permeability. CYP450 inhibition was isoform dependent, with 2C19 and 3A4 particularly susceptible, and the majority of compounds tested against rat and human microsomes were metabolized rapidly. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.024
• 作为产物：
  描述：

  2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)ethan-1-ol 在 ruthenium(III) trichloride hydrate 、 高碘酸 作用下， 以96%的产率得到2-(3-methyl-1,2-dioxaspiro[4.5]decan-3-yl)acetic acid
  参考文献：
  名称：

  Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.10.083