benzyl 2-[(3S,6S)-6-((E)-3-oxo-3-phenylprop-1-enyl)-1,2-dioxan-3-yl]acetate

• 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: benzyl 2-[(3S,6S)-6-((E)-3-oxo-3-phenylprop-1-enyl)-1,2-dioxan-3-yl]acetate
• 英文别名: benzyl 2-[(3S,6S)-6-[(E)-3-oxo-3-phenylprop-1-enyl]dioxan-3-yl]acetate
• 化学式: C₂₂H₂₂O₅
• 分子量: 366.414
• InChiKey: AMBLUZQNNGVSFX-JAPHFTBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-己烯-1-醇 在 草酰氯 、 二甲基硫 、 氧气 、 tetraphenylporphyrin 、 臭氧 、 二甲基亚砜 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 34.03h， 生成 benzyl 2-[(3S,6S)-6-((Z)-3-oxo-3-phenylprop-1-enyl)-1,2-dioxan-3-yl]acetate 、 benzyl 2-[(3S,6S)-6-((E)-3-oxo-3-phenylprop-1-enyl)-1,2-dioxan-3-yl]acetate
  参考文献：
  名称：

  Synthesis of antitrypanosomal 1,2-dioxane derivatives based on a natural product scaffold

  摘要：

  A short practical synthesis of a new natural product based scaffold (6), based on antitrypanosomal and antimalarial compounds isolated from different Plakortis species is described. The scaffold contains a peroxide unit that is surprisingly stable to chemical manipulation elsewhere in the molecule, enabling it to be elaborated into a small library of derivatives. It is stable to ozonolysis, reductive work-up with dimethylsulfide and the Wittig reaction with stabilized phosphorus ylides. The scaffold along with its Wittig analogues has displayed low to sub-micro molar (0.2-3.3 mu M) antitrypanosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.059

文献信息

• Synthesis of antitrypanosomal 1,2-dioxane derivatives based on a natural product scaffold
  作者：Harish Holla、Mehdi Labaied、Ngoc Pham、Ian D. Jenkins、Kenneth Stuart、Ronald J. Quinn

  DOI：10.1016/j.bmcl.2011.06.059

  日期：2011.8

  A short practical synthesis of a new natural product based scaffold (6), based on antitrypanosomal and antimalarial compounds isolated from different Plakortis species is described. The scaffold contains a peroxide unit that is surprisingly stable to chemical manipulation elsewhere in the molecule, enabling it to be elaborated into a small library of derivatives. It is stable to ozonolysis, reductive work-up with dimethylsulfide and the Wittig reaction with stabilized phosphorus ylides. The scaffold along with its Wittig analogues has displayed low to sub-micro molar (0.2-3.3 mu M) antitrypanosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.