3-cyclohex-1-enyl-1-pyridin-2-yl-prop-2-yn-1-ol | 934399-73-2

• 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-cyclohex-1-enyl-1-pyridin-2-yl-prop-2-yn-1-ol
• CAS: 934399-73-2
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: LXDHKVVMYCPOSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33.12
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-cyclohex-1-enyl-1-pyridin-2-yl-prop-2-yn-1-ol 在 4-二甲氨基吡啶 、 indium(III) chloride 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 3-(1-cyclohexenyl)indolizin-1-yl pivalate
  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
• 作为产物：
  描述：

  吡啶-2-甲醛 、 (cyclohex-1-en-1-ylethynyl)magnesium bromide 生成 3-cyclohex-1-enyl-1-pyridin-2-yl-prop-2-yn-1-ol
  参考文献：
  名称：

  通过过渡金属催化的环异构化方案形成多取代的 N-稠合杂环。

  摘要：

  已经开发了两种用于组装多取代 N-稠合杂环的互补方案。结果表明，1,3-二取代的 N-稠合杂环，包括中氮茚、吡咯并喹喔啉和吡咯并噻唑，可以通过一种极其温和且有效的方法轻松合成，该方法涉及新型银催化含炔丙基杂环的环化聚合。或者，可以通过涉及炔烃-亚乙烯基异构化以及伴随的氢、甲硅烷基、甲锡烷基或甲锗烷基基团的1,2-位移的新型级联转化来获得1,2-二取代的杂环。这种温和而简单的方法可以选择性且高效地合成中氮茚、吡咯并异喹啉、吡咯并喹喔啉、吡咯并吡嗪和吡咯并噻唑。

  DOI：

  10.1016/j.tet.2008.04.023

文献信息

• Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring
  作者：Dmitri Chernyak、Cathy Skontos、Vladimir Gevorgyan

  DOI：10.1021/ol1011949

  日期：2010.7.16

  An efficient two-component palladium-catalyzed arylation/cyclization cascade approach toward a variety of N-fused pyrroloheterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with propargylic esters or ethers followed by the 5-endo-dig cyclization leading to highly functionalized pyrroloheterocycles in good to excellent yield.

  一种有效的双组分钯催化芳基化/环化级联方法已被开发用于各种 N 稠合吡咯杂环。这种转化通过芳基卤化物与炔丙酯或醚的钯催化偶联进行，然后进行 5 - end -dig环化，产生高度官能化的吡咯杂环，收率良好至极好。
• Synthesis of Indolizine Derivatives by Pd-Catalyzed Oxidative Carbonylation
  作者：Tongyu Xu、Howard Alper

  DOI：10.1021/acs.orglett.5b02220

  日期：2015.9.18

  An efficient synthesis of indolizine derivatives by palladium-catalyzed oxidative carbonylation of propargylic pyridines has been developed. The reaction can be conducted at room temperature and under 3 bar of CO in the presence of Pd2(dba)3 or Pd/C. The catalyst Pd/C could be easily removed from the reaction and recycled.

  已经开发了通过钯催化的炔丙基吡啶的氧化羰基化来有效合成吲哚嗪衍生物。该反应可以在室温下和在3巴的CO下，在Pd 2（dba）3或Pd / C存在下进行。催化剂Pd / C可以容易地从反应中除去并再循环。
• Base- and Ligand-free Room-Temperature Synthesis of N-Fused Heteroaromatic Compounds via the Transition Metal-Catalyzed Cycloisomerization Protocol
  作者：Ilya V. Seregin、Alex W. Schammel、Vladimir Gevorgyan

  DOI：10.1021/ol701464j

  日期：2007.8.1

  A new practical method for the synthesis of N-fused heterocycles via the transition metal-catalyzed cycloisomerization of heterocyles possessing a propagyl group has been developed. This very mild, base- and ligand-free method allows for the synthesis of diverse fused heterocyclic cores in good to excellent yields.
• 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.
• Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones
  作者：Eric M. Bunnelle、Cameron R. Smith、Sharon K. Lee、Surendra W. Singaram、Allison J. Rhodes、Richmond Sarpong

  DOI：10.1016/j.tet.2008.02.103

  日期：2008.7

  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.