1-(quinolin-2-yl)hept-2-ynyl pivalate | 934399-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(quinolin-2-yl)hept-2-ynyl pivalate
• CAS: 934399-75-4
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: WKEYYCYMOZMMEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(quinolin-2-yl)hept-2-ynyl pivalate 在 platinum(II) chloride 2-(二叔丁基膦)联苯 作用下， 以 苯 为溶剂， 反应 4.0h， 以88%的产率得到1-butylpyrrolo[1,2-a]quinolin-3-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：

  喹啉-2-甲醛 在 4-二甲氨基吡啶 、 乙基溴化镁 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 1-(quinolin-2-yl)hept-2-ynyl pivalate
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylative Cyclization/Arylation Cascade for 2-Aroylindolizine Synthesis

  摘要：

  An efficient synthesis of densely substituted 2-aroylindolizines via the palladium-catalyzed carbonylative cyclization/arylation is reported. This transformation proceeds via the 5-endo-dig cyclization of 2-propargylpyridine triggered by an aroyl Pd complex. It produced diversely substituted 2-aroylindolizines in good to excellent yields.

  DOI：

  10.1021/ol302947r

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。
• 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.