14-[tert-butyl-dimethylsilyloxy]melampolide | 680202-82-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 14-[tert-butyl-dimethylsilyloxy]melampolide
• CAS: 680202-82-8
• 化学式: C₂₁H₃₄O₃Si
• 分子量: 362.585
• InChiKey: MKJAYTCCBORWJV-MYISNJMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  14-[tert-butyl-dimethylsilyloxy]melampolide 在 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到14-oxomelampolide
  参考文献：
  名称：

  Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models

  摘要：

  The comparative study between the theoretical molecular properties of the starting materials and the yields in the transformation of melampolides to cis,cis-germacranolides using SeO2/t-BuOOH (TBHP) as oxidant allows to establish a feasible relationship with their values of dipolar moment. Conditions for this transformation are optimized and some mechanistic considerations are made based in this finding. Cluster analysis of the phytotoxic activity of the melampolides and cis, cis-germacranolides obtained shows that the activity is greatly influenced by the spatial shape of the backbone, prevailing upon other factors such as the presence of reactive functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.128
• 作为产物：
  描述：

  木香烃内酯 在 2,3,5-三甲基吡啶 、 叔丁基过氧化氢 、 selenium(IV) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 14-[tert-butyl-dimethylsilyloxy]melampolide
  参考文献：
  名称：

  Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models

  摘要：

  The comparative study between the theoretical molecular properties of the starting materials and the yields in the transformation of melampolides to cis,cis-germacranolides using SeO2/t-BuOOH (TBHP) as oxidant allows to establish a feasible relationship with their values of dipolar moment. Conditions for this transformation are optimized and some mechanistic considerations are made based in this finding. Cluster analysis of the phytotoxic activity of the melampolides and cis, cis-germacranolides obtained shows that the activity is greatly influenced by the spatial shape of the backbone, prevailing upon other factors such as the presence of reactive functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.128