(E)-3-hydroxy-5-phenyl-1-(2-pyridyl)-4-penten-1-yne | 905946-14-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-3-hydroxy-5-phenyl-1-(2-pyridyl)-4-penten-1-yne
• 英文别名: (e)-3-Hydroxy-5-phenyl-1-(2-pyridyl)-4-penten-1-yne；(E)-1-phenyl-5-pyridin-2-ylpent-1-en-4-yn-3-ol
• CAS: 905946-14-7
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: KNZUUUZVHRKYHO-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-hydroxy-5-phenyl-1-(2-pyridyl)-4-penten-1-yne 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(E)-3-oxo-5-phenyl-1-(2-pyridyl)-4-penten-1-yne
  参考文献：
  名称：

  Synthesis of unsymmetrically 2,6-disubstituted 2,3-dihydrothiopyran-4-ones

  摘要：

  A series of 2,3-dihydrothiopyran-4-one derivatives with unequal substituents in the 2- and 6-position have been prepared by double conjugate addition of sulfide to enynones. These starting materials were accessed in two steps from terminal alkynes and alpha,beta-unsaturated aldehydes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.080
• 作为产物：
  描述：

  2-乙炔基吡啶 、 肉桂醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 (E)-3-hydroxy-5-phenyl-1-(2-pyridyl)-4-penten-1-yne
  参考文献：
  名称：

  Electronic Effects in the Pt-Catalyzed Cycloisomerization of Propargylic Esters:  Synthesis of 2,3-Disubstituted Indolizines as a Mechanistic Probe

  摘要：

  [GRAPHICS]The initial 5-exo versus 6-endo cyclization of the acyl group onto the activated alkyne of propargylic esters has been found to be dependent on electronic effects of the acyl, alkyne, and propargylic carbon substituents. These electronic effects control the ratio of 2,3-disubstituted versus 1,3-disubstituted indolizine products formed when substrates bearing pyridines at the alkyne terminus are used.

  DOI：

  10.1021/ol701973s

文献信息

• Electronic Effects in the Pt-Catalyzed Cycloisomerization of Propargylic Esters:  Synthesis of 2,3-Disubstituted Indolizines as a Mechanistic Probe
  作者：Alison R. Hardin、Richmond Sarpong

  DOI：10.1021/ol701973s

  日期：2007.10.1

  [GRAPHICS]The initial 5-exo versus 6-endo cyclization of the acyl group onto the activated alkyne of propargylic esters has been found to be dependent on electronic effects of the acyl, alkyne, and propargylic carbon substituents. These electronic effects control the ratio of 2,3-disubstituted versus 1,3-disubstituted indolizine products formed when substrates bearing pyridines at the alkyne terminus are used.
• Synthesis of unsymmetrically 2,6-disubstituted 2,3-dihydrothiopyran-4-ones
  作者：Anna Rosiak、Jens Christoffers

  DOI：10.1016/j.tetlet.2006.05.080

  日期：2006.7

  A series of 2,3-dihydrothiopyran-4-one derivatives with unequal substituents in the 2- and 6-position have been prepared by double conjugate addition of sulfide to enynones. These starting materials were accessed in two steps from terminal alkynes and alpha,beta-unsaturated aldehydes. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of 2,3-Dihydrothiopyran-4-ones from 3-Oxo-1-pentene-4-ynes
  作者：Anna Rosiak、Ralf M. Müller、Jens Christoffers

  DOI：10.1007/s00706-006-0571-4

  日期：2007.1

  3-Oxo-1-pentene-4-ynes were converted with sodium sulfide or hydrogensulfide to give 2,6-disubstituted 2,3-dihydrothiopyran-4-one derivatives. The starting materials were prepared in two steps from terminal alkynes and alpha,beta-unsaturated aldehydes.