20-(4-hydroxyphenyl)-1-eicosyne | 223726-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 20-(4-hydroxyphenyl)-1-eicosyne
• 英文别名: 4-Icos-19-ynylphenol
• CAS: 223726-39-4
• 化学式: C₂₆H₄₂O
• 分子量: 370.619
• InChiKey: HEKPDRSMAMJPMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  20-(4-hydroxyphenyl)-1-eicosyne 在 咪唑 、 4-二甲氨基吡啶 、 二氯二茂锆 、 甲基锂 、 三甲基铝 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (2R,3E)-methyl 22-(4-tert-butyldiphenylsiloxyphenyl)-2,4-dimethyldocos-3-enoate
  参考文献：
  名称：

  Synthesis of Elenic Acid, an Inhibitor of Topoisomerase II

  摘要：

  A short, efficient synthesis of elenic acid, a marine natural product with interesting biological activity, has been completed. Critical features of the synthesis are the development of methodology for the one-pot elaboration of an alkyne to an (E)-beta,gamma-unsaturated ester with a stereocenter at the alpha-position and the use of the zipper reaction of a 1-arylalkyne. This reaction has not been previously reported with aromatic substrates. The synthesis strategy provides considerable flexibility for the preparation of structural analogues.

  DOI：

  10.1021/jo982260t
• 作为产物：
  描述：

  1-二十一碳炔 在 copper(l) iodide 、 tris(triphenylphosphano)palladium 、 potassium tert-butylate 、 lithium 、 1,3-丙二胺 、 二异丙胺 作用下， 反应 35.0h， 生成 20-(4-hydroxyphenyl)-1-eicosyne
  参考文献：
  名称：

  Synthesis of Elenic Acid, an Inhibitor of Topoisomerase II

  摘要：

  A short, efficient synthesis of elenic acid, a marine natural product with interesting biological activity, has been completed. Critical features of the synthesis are the development of methodology for the one-pot elaboration of an alkyne to an (E)-beta,gamma-unsaturated ester with a stereocenter at the alpha-position and the use of the zipper reaction of a 1-arylalkyne. This reaction has not been previously reported with aromatic substrates. The synthesis strategy provides considerable flexibility for the preparation of structural analogues.

  DOI：

  10.1021/jo982260t

文献信息

• Synthesis of Elenic Acid, an Inhibitor of Topoisomerase II
  作者：Rebecca C. Hoye、Alejandro S. Baigorria、Michael E. Danielson、Alexa A. Pragman、Hemaka A. Rajapakse

  DOI：10.1021/jo982260t

  日期：1999.4.1

  A short, efficient synthesis of elenic acid, a marine natural product with interesting biological activity, has been completed. Critical features of the synthesis are the development of methodology for the one-pot elaboration of an alkyne to an (E)-beta,gamma-unsaturated ester with a stereocenter at the alpha-position and the use of the zipper reaction of a 1-arylalkyne. This reaction has not been previously reported with aromatic substrates. The synthesis strategy provides considerable flexibility for the preparation of structural analogues.