2-(octadec-3-ynyl)-1,3-dioxolane | 1186603-72-4

• 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-(octadec-3-ynyl)-1,3-dioxolane
• CAS: 1186603-72-4
• 化学式: C₂₁H₃₈O₂
• 分子量: 322.532
• InChiKey: LGDAPJBXZZZSCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  23.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(octadec-3-ynyl)-1,3-dioxolane 在 氨 、 lithium 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到2-((E)-octadec-3-enyl)-1,3-dioxolane
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of cis-Uvariamicin I and cis-Reticulatacin

  摘要：

  Diastereoisomeric mixtures of cis-uvariamicin I (15R,16R,19S,20S,36S and 15S,16S,19R,20R,36S) and cis-reticulatacin (17R, 18R,21S,22S,36S and 17S,18S,21R,22 R,36S) were synthesized to determine the stereochemistry of the natural products isolated from Annona muricata. It was not possible to resolve I mixture of the four synthetic isomers using chiral HPLC, but the mixed isomers could be distinguished using chiral HPLC EIMS with extracted fragment ion analysis. Comparison of synthetic standards with the natural isolate revealed that cis-uvariamicin I and cis-reticulatacin are present in nature as Mixtures of threo-cis-threo diastereoisomers. It is suggested that the nomenclature for the natural products is amended as follows: (15R,16R,19S,20S,36S)-cis-uvariamicin I (cis-uvaramicin IA); (15S,16S,19R,20R,36S)-cis-uvariamicin I (cis-uvariamicin IB); (17R,18R,21S,22S,36S)-cis-reticulatacin (cis-reticulatacin A); (17S,18S,21R,22R,36S)-cis-reticulatacin (cis-reticulatacin B).

  DOI：

  10.1021/jo9012578
• 作为产物：
  描述：

  2-(but-3-yn-1-yl)-1,3-dioxolane 、 溴代十四烷 在 正丁基锂 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.67h， 以80%的产率得到2-(octadec-3-ynyl)-1,3-dioxolane
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of cis-Uvariamicin I and cis-Reticulatacin

  摘要：

  Diastereoisomeric mixtures of cis-uvariamicin I (15R,16R,19S,20S,36S and 15S,16S,19R,20R,36S) and cis-reticulatacin (17R, 18R,21S,22S,36S and 17S,18S,21R,22 R,36S) were synthesized to determine the stereochemistry of the natural products isolated from Annona muricata. It was not possible to resolve I mixture of the four synthetic isomers using chiral HPLC, but the mixed isomers could be distinguished using chiral HPLC EIMS with extracted fragment ion analysis. Comparison of synthetic standards with the natural isolate revealed that cis-uvariamicin I and cis-reticulatacin are present in nature as Mixtures of threo-cis-threo diastereoisomers. It is suggested that the nomenclature for the natural products is amended as follows: (15R,16R,19S,20S,36S)-cis-uvariamicin I (cis-uvaramicin IA); (15S,16S,19R,20R,36S)-cis-uvariamicin I (cis-uvariamicin IB); (17R,18R,21S,22S,36S)-cis-reticulatacin (cis-reticulatacin A); (17S,18S,21R,22R,36S)-cis-reticulatacin (cis-reticulatacin B).

  DOI：

  10.1021/jo9012578