6-(5-cholesten-3β-yloxy)-3-hexyne iodide | 75014-51-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6-(5-cholesten-3β-yloxy)-3-hexyne iodide
• CAS: 75014-51-6
• 化学式: C₃₃H₅₃IO
• 分子量: 592.688
• InChiKey: UURNFKUOCHGXOD-IJXDZZBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.63
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  6-(5-cholesten-3β-yloxy)-3-hexyne iodide 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-((6-((10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)hex-3-yn-1-yl)thio)-6-methyltetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Glycolipids as potential immunologic adjuvants

  摘要：

  A group of 1-thio-beta-L-fucopyranosides containing hexadecane, 9-octadecene, adamantane, 1,2-diphenyltetrafluoroethane, and 3-hexynyl- and 3,6-dioxaoctylcholesterols were synthesized as potential immunologic adjuvants. Many of these fucosyl lipids and 6-(5-cholesten-3 beta-yloxy)hexyl 1 thioglycosides were found to give good response to subunit A/Victoria influenza virus. Carbohydrates with L-fucose and D-galactose backbones appeared essential for adjuvant activity. Lactose which has a terminal D-galactose moiety was found to be active, whereas L-arabinose which lacks a 5-(hydroxymethyl) group was inactive.

  DOI：

  10.1021/jm00185a007
• 作为产物：
  描述：

  2-(5-cholesten-3β-yloxy)ethyl iodide 在 吡啶 、 苯基锂 、 sodium iodide 作用下， 以 1,4-二氧六环 、 丁酮 为溶剂， 反应 12.0h， 生成 6-(5-cholesten-3β-yloxy)-3-hexyne iodide
  参考文献：
  名称：

  Glycolipids as potential immunologic adjuvants

  摘要：

  A group of 1-thio-beta-L-fucopyranosides containing hexadecane, 9-octadecene, adamantane, 1,2-diphenyltetrafluoroethane, and 3-hexynyl- and 3,6-dioxaoctylcholesterols were synthesized as potential immunologic adjuvants. Many of these fucosyl lipids and 6-(5-cholesten-3 beta-yloxy)hexyl 1 thioglycosides were found to give good response to subunit A/Victoria influenza virus. Carbohydrates with L-fucose and D-galactose backbones appeared essential for adjuvant activity. Lactose which has a terminal D-galactose moiety was found to be active, whereas L-arabinose which lacks a 5-(hydroxymethyl) group was inactive.

  DOI：

  10.1021/jm00185a007