8-Phenylmethoxyoct-5-yne-1,4-diol | 1449106-90-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-Phenylmethoxyoct-5-yne-1,4-diol
• 英文别名: 8-phenylmethoxyoct-5-yne-1,4-diol
• CAS: 1449106-90-4
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: XUVSXLNRZYXZQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-Phenylmethoxyoct-5-yne-1,4-diol 在 mercuric triflate 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Stereoselectivity of electrophile-promoted oxacyclizations of 1,4-dihydroxy-5-alkenes to 3-hydroxytetrahydropyrans

  摘要：

  Stereoinduction from the allylic hydroxyl group of 1,4-dihydroxy-5-alkenes has been systematically explored with various alkene substitution patterns and electrophilic reagents. For formation of erythro-diastereomers of 2-substituted 3-hydroxytetrahydropyrans, mercuric trifluoroacetate-promoted cyclizations of cis- and (Z)-alkenyldiols generally give the highest diastereoselectivities. For the corresponding 1,4-dihydroxy-5-alkyne, mercuric triflate-catalyzed cyclization followed by triethylsilane reduction affords an alternative route to the euthro-diastereomer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.138
• 作为产物：
  描述：

  ((but-3-yn-1-yloxy)methyl)benzene 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.08h， 生成 8-Phenylmethoxyoct-5-yne-1,4-diol
  参考文献：
  名称：

  Stereoselectivity of electrophile-promoted oxacyclizations of 1,4-dihydroxy-5-alkenes to 3-hydroxytetrahydropyrans

  摘要：

  Stereoinduction from the allylic hydroxyl group of 1,4-dihydroxy-5-alkenes has been systematically explored with various alkene substitution patterns and electrophilic reagents. For formation of erythro-diastereomers of 2-substituted 3-hydroxytetrahydropyrans, mercuric trifluoroacetate-promoted cyclizations of cis- and (Z)-alkenyldiols generally give the highest diastereoselectivities. For the corresponding 1,4-dihydroxy-5-alkyne, mercuric triflate-catalyzed cyclization followed by triethylsilane reduction affords an alternative route to the euthro-diastereomer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.138

文献信息

• Stereoselectivity of electrophile-promoted oxacyclizations of 1,4-dihydroxy-5-alkenes to 3-hydroxytetrahydropyrans
  作者：Frank E. McDonald、Kento Ishida、Jessica A. Hurtak

  DOI：10.1016/j.tet.2013.04.138

  日期：2013.9

  Stereoinduction from the allylic hydroxyl group of 1,4-dihydroxy-5-alkenes has been systematically explored with various alkene substitution patterns and electrophilic reagents. For formation of erythro-diastereomers of 2-substituted 3-hydroxytetrahydropyrans, mercuric trifluoroacetate-promoted cyclizations of cis- and (Z)-alkenyldiols generally give the highest diastereoselectivities. For the corresponding 1,4-dihydroxy-5-alkyne, mercuric triflate-catalyzed cyclization followed by triethylsilane reduction affords an alternative route to the euthro-diastereomer. (C) 2013 Elsevier Ltd. All rights reserved.