(+/-)-3-(pyridin-2-yl)non-4-yn-3-ol | 934399-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (+/-)-3-(pyridin-2-yl)non-4-yn-3-ol
• 英文别名: 3-Pyridin-2-ylnon-4-yn-3-ol
• CAS: 934399-86-7
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: WRDVSBHVDXAKNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (+/-)-3-(pyridin-2-yl)non-4-yn-3-ol 在 platinum(II) chloride caesium carbonate 、 2-(二叔丁基膦)联苯 作用下， 以 苯 为溶剂， 反应 48.0h， 以66%的产率得到(+/-)-3-butyl-8a-ethylindolizin-1(8aH)-one
  参考文献：
  名称：

  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones

  摘要：

  Several heterocycles such as furanones, pyrrolones, and indolizines, which are of pharmacological importance, are easily accessed via the Pt(II)-catalyzed heterocyclization/1,2-migration of propargylic ketols or hydroxy imine derivatives. This method sidesteps the challenges of traditional heteroaromatic oxygenation strategies such as regioselectivity and functional group tolerance in the syntheses of these heterocycles. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.103
• 作为产物：
  描述：

  1-(pyridin-2-yl)hept-2-yn-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (+/-)-3-(pyridin-2-yl)non-4-yn-3-ol
  参考文献：
  名称：

  Pt-Catalyzed Cyclization/1,2-Migration for the Synthesis of Indolizines, Pyrrolones, and Indolizinones

  摘要：

  Indolizine, pyrrolone, and indolizinone heterocycles are easily accessed via the Pt(II)-catalyzed cycloisomerization or a tandem cyclization/1,2-migration of pyridine propargylic alcohols and derivatives. This method provides an efficient synthesis of highly functionalized heterocycles from readily available substrates.

  DOI：

  10.1021/ol0701971

文献信息

• Highly Efficient Synthesis of Functionalized Indolizines and Indolizinones by Copper-Catalyzed Cycloisomerizations of Propargylic Pyridines
  作者：Bin Yan、Yebing Zhou、Hao Zhang、Jingjin Chen、Yuanhong Liu

  DOI：10.1021/jo070983j

  日期：2007.9.1

  [GRAPHICS]The copper-catalyzed cycloisomerizations of 2-pyridyl-substituted propargylic acetates and its derivatives are described, which offer an efficient route to C-1 oxygenated indolizines with a wide range of substituents under mild reaction conditions. The presented method could be readily applied to the synthesis of indolizinones through a cyclization/1,2-migration of tertiary propargylic alcohols.