α-(O-undecan-2-ynyl)-ω-(O-propargyl)diethylene glycol | 286466-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(O-undecan-2-ynyl)-ω-(O-propargyl)diethylene glycol
• 英文别名: 1-[2-(2-Prop-2-ynoxyethoxy)ethoxy]undec-2-yne
• CAS: 286466-92-0
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: GMISSDWYKXJHQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(O-undecan-2-ynyl)-ω-(O-propargyl)diethylene glycol 在 platinum(IV) oxide 正丁基锂 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 26.25h， 生成 (5S)-3-[8-hydroxy-12-[2-(2-undecoxyethoxy)ethoxy]dodecyl]-4-(methoxymethoxy)-5-methyloxolan-2-one
  参考文献：
  名称：

  Polyether Mimics of Naturally Occurring Cytotoxic Annonaceous Acetogenins

  摘要：

  On the basis of the ionophore model, polyether analogues 4 and 6 were designed and synthesized to mimic the naturally occurring annonaceous acetogenins corossolin (2) and bullatin (5), which were discovered as members of a large family of novel polyketides with cytotoxicity, antitumoral, and other biological activities since 1982. The preliminary screening shows that they have compatible cytotoxicity with the corresponding natural annonaceous acetogenins. These results open a potential way to find more active antitumor agents with simplified structures based on natural annonaceous acetogenins.

  DOI：

  10.1021/jm990575a
• 作为产物：
  描述：

  1-溴辛烷 、 二乙二醇双(2-丙炔基)醚 在 正丁基锂 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.5h， 以41.7%的产率得到α-(O-undecan-2-ynyl)-ω-(O-propargyl)diethylene glycol
  参考文献：
  名称：

  Polyether Mimics of Naturally Occurring Cytotoxic Annonaceous Acetogenins

  摘要：

  On the basis of the ionophore model, polyether analogues 4 and 6 were designed and synthesized to mimic the naturally occurring annonaceous acetogenins corossolin (2) and bullatin (5), which were discovered as members of a large family of novel polyketides with cytotoxicity, antitumoral, and other biological activities since 1982. The preliminary screening shows that they have compatible cytotoxicity with the corresponding natural annonaceous acetogenins. These results open a potential way to find more active antitumor agents with simplified structures based on natural annonaceous acetogenins.

  DOI：

  10.1021/jm990575a

文献信息

• Polyether Mimics of Naturally Occurring Cytotoxic Annonaceous Acetogenins
  作者：Zhu-Jun Yao、Hai-Ping Wu、Yu-Lin Wu

  DOI：10.1021/jm990575a

  日期：2000.6.1

  On the basis of the ionophore model, polyether analogues 4 and 6 were designed and synthesized to mimic the naturally occurring annonaceous acetogenins corossolin (2) and bullatin (5), which were discovered as members of a large family of novel polyketides with cytotoxicity, antitumoral, and other biological activities since 1982. The preliminary screening shows that they have compatible cytotoxicity with the corresponding natural annonaceous acetogenins. These results open a potential way to find more active antitumor agents with simplified structures based on natural annonaceous acetogenins.