2-(5-hydroxypent-3-yn-1-yl)phenol | 1360054-31-4

• 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: 2-(5-hydroxypent-3-yn-1-yl)phenol
• 英文别名: 2-(5-hydroxypent-3-ynyl)phenol
• CAS: 1360054-31-4
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: FOOGNCVYBXDJQX-UHFFFAOYSA-N

物化性质

• 沸点：
  357.9±27.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-hydroxypent-3-yn-1-yl)phenol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 红铝 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (E)-5-(2-hydroxyphenyl)pent-2-enyl 2,2,2-trichloroacetimidate
  参考文献：
  名称：

  Palladium(II)-Catalyzed Enantioselective Synthesis of 2-Vinyl Oxygen Heterocycles

  摘要：

  2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc](2)-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn-deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.

  DOI：

  10.1021/jo202553a
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 正丁基锂 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.66h， 生成 2-(5-hydroxypent-3-yn-1-yl)phenol
  参考文献：
  名称：

  Synthesis of Desfluorinated Nebivolol Isomers

  摘要：

  The syntheses of all possible stereoisomers of desfluorinated side products of the potent antihypertensive beta-blocker nebivolol are reported. A straightforward approach using a common racemic precursor was employed to obtain the desired optically active building blocks. For one series of compounds, a Sharpless asymmetric epoxidation (SAE) route yielded in a direct fashion the required compounds whereas a Mitsunobu reaction was selected to obtain the other series of compounds. This offers a flexible approach to all desfluoronebivolol side-products in order to fully characterize them.

  DOI：

  10.1021/acs.joc.5b00263

文献信息

• Palladium(II)-Catalyzed Enantioselective Synthesis of 2-Vinyl Oxygen Heterocycles
  作者：Jeffrey S. Cannon、Angela C. Olson、Larry E. Overman、Nicole S. Solomon

  DOI：10.1021/jo202553a

  日期：2012.2.17

  2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc](2)-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn-deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.
• Synthesis of Desfluorinated Nebivolol Isomers
  作者：Purushothama Chary Khandavalli、Oliver Spiess、Oliver M. Böhm、Ilia Freifeld、Kurt Kesseler、Gerhard Jas、Dieter Schinzer

  DOI：10.1021/acs.joc.5b00263

  日期：2015.4.17

  The syntheses of all possible stereoisomers of desfluorinated side products of the potent antihypertensive beta-blocker nebivolol are reported. A straightforward approach using a common racemic precursor was employed to obtain the desired optically active building blocks. For one series of compounds, a Sharpless asymmetric epoxidation (SAE) route yielded in a direct fashion the required compounds whereas a Mitsunobu reaction was selected to obtain the other series of compounds. This offers a flexible approach to all desfluoronebivolol side-products in order to fully characterize them.