(2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-hydroxy-3-butyn-4-yl)tetrahydrofuran | 851532-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-hydroxy-3-butyn-4-yl)tetrahydrofuran
• CAS: 851532-61-1
• 化学式: C₁₅H₁₇FO₃
• 分子量: 264.297
• InChiKey: YBHSOHNEXQXKEO-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-hydroxy-3-butyn-4-yl)tetrahydrofuran 在 ammonium hydroxide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-[N-hydroxyureidyl]-3-butyn-4-yl)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective synthesis of chiral tetrahydrofurans with potent 5-LO inhibitory activity

  摘要：

  Chiral glyceraldehydes have been exploited for the design of convenient and scalable synthetic approaches to chiral tetrahydrofurans, which have potential as potent 5-lipoxygenase (5-LO) inhibitors. The synthesis of all four possible stereoisomers by a general methodology is reported; wherein the chirons derived from the glyceraldehyde derivatives on reaction with homopropargyl ether, cyclization and further reactions gave the targets. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.045
• 作为产物：
  描述：

  (2R)-5-hydroxy-1,2-(isopropylidenedioxy)-9-(4-methoxybenzyloxy)non-6-yne 在 4-二甲氨基吡啶 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 (2R,5R)-trans-5-((4-fluorophenoxy)methyl)-2-(1-hydroxy-3-butyn-4-yl)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective synthesis of chiral tetrahydrofurans with potent 5-LO inhibitory activity

  摘要：

  Chiral glyceraldehydes have been exploited for the design of convenient and scalable synthetic approaches to chiral tetrahydrofurans, which have potential as potent 5-lipoxygenase (5-LO) inhibitors. The synthesis of all four possible stereoisomers by a general methodology is reported; wherein the chirons derived from the glyceraldehyde derivatives on reaction with homopropargyl ether, cyclization and further reactions gave the targets. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.045