1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2(Z),5(Z),8(Z)-triene | 98582-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2(Z),5(Z),8(Z)-triene
• 英文别名: 1-[(3,4,5,6-tetrahydro-2-pyranyl)oxy]tetradeca-2(Z),5(Z),8(Z)-triene；2-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienoxy]oxane
• CAS: 98582-22-0
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: GTRZCMUXVUJHEY-DPRXULCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2(Z),5(Z),8(Z)-triene 在 溴 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 diethyl 2(Z),5(Z),8(Z)-tetradecatrienylphosphonate
  参考文献：
  名称：

  Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid analogs

  摘要：

  A series of eicosatetraenes (2-24) were designed, synthesized, and evaluated in vitro for inhibitory activity against 5-lipoxygenase (20000g supernatant from homogenized rat basophilic leukemia cells). All compounds were found to be active with the potencies (IC50's) ranging from 0.19 to 97 microM. Compounds containing the hydroxamic acid functionality (10-12) exhibited the best activity (IC50 = 0.19-2.8 microM). The most potent inhibitor was 5-[(hydroxyamino)carbonyl]methyl]-6,8,11,14-eicosatetraenoic acid (11), which was 10 times more active than the C-1 hydroxamates of arachidonic acid or 5-HETE. Cyclization of the linear eicosanoids 2 and 14 in the C-1 to C-5 region produced compounds (21 and 24, respectively) with several-fold greater potency.

  DOI：

  10.1021/jm00390a010
• 作为产物：
  描述：

  1-bromo-2,5-undecadiyne 在 喹啉 、 Pd-BaSO₄ copper(l) iodide 、 乙基溴化镁 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 12.75h， 生成 1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2(Z),5(Z),8(Z)-triene
  参考文献：
  名称：

  Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid analogs

  摘要：

  A series of eicosatetraenes (2-24) were designed, synthesized, and evaluated in vitro for inhibitory activity against 5-lipoxygenase (20000g supernatant from homogenized rat basophilic leukemia cells). All compounds were found to be active with the potencies (IC50's) ranging from 0.19 to 97 microM. Compounds containing the hydroxamic acid functionality (10-12) exhibited the best activity (IC50 = 0.19-2.8 microM). The most potent inhibitor was 5-[(hydroxyamino)carbonyl]methyl]-6,8,11,14-eicosatetraenoic acid (11), which was 10 times more active than the C-1 hydroxamates of arachidonic acid or 5-HETE. Cyclization of the linear eicosanoids 2 and 14 in the C-1 to C-5 region produced compounds (21 and 24, respectively) with several-fold greater potency.

  DOI：

  10.1021/jm00390a010

文献信息

• 1,2-bis(diphenylphosphino)ethane tetrahalide: A convenient reagent for the conversion of alcohols to the corresponding halides
  作者：Steven P. Schmidt、Dee W. Brooks

  DOI：10.1016/s0040-4039(01)80984-9

  日期：1987.1

  rapid conversion under mild conditions of various alcohols and tetrahydro-2-pyranyl (THP) protected alcohols into the corresponding halide (Br or I) are described using the corresponding 1,2-bis (triphenylphosphino)ethane tetrahalide. Tert-butyldimethylsilyl ethers, esters and olefins are stable to these conditions.

  描述了使用相应的1,2-双（三苯基膦基）乙烷四卤化物，在温和条件下将各种醇和四氢-2-吡喃基（THP）保护的醇高效快速转化为相应的卤化物（Br或I）。叔丁基二甲基甲硅烷基醚，酯和烯烃对这些条件稳定。
• Eicosatetraenehydroxamates: inhibitors of 5-lipoxygenase
  作者：F.A.J. Kerdesky、J.H. Holms、S.P. Schmidt、R.O. Dyer、G.W. Carter

  DOI：10.1016/s0040-4039(00)98946-9

  日期：1985.1
• GUZMAN, ANGEL;MUCHOWSKI, JOSEPH M.
  作者：GUZMAN, ANGEL、MUCHOWSKI, JOSEPH M.

  DOI：——

  日期：——
• SCHMIDT S. P.; BROOKS D. W., TETRAHEDRON LETT., 28,(1987) N 7, 767-768
  作者：SCHMIDT S. P.、 BROOKS D. W.

  DOI：——

  日期：——