3-Cyclopropyl-1-pyridin-2-ylprop-2-yn-1-ol | 934399-69-6

• 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-Cyclopropyl-1-pyridin-2-ylprop-2-yn-1-ol
• CAS: 934399-69-6
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: BBIVAWPAYMLFHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-Cyclopropyl-1-pyridin-2-ylprop-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 6.0h， 生成 3-cyclopropylindolizin-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 、 环丙乙炔 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以81%的产率得到3-Cyclopropyl-1-pyridin-2-ylprop-2-yn-1-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

• 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.
• Palladium-Catalyzed Intramolecular Carbopalladation/Cyclization Cascade: Access to Polycyclic N-Fused Heterocycles
  作者：Dmitri Chernyak、Vladimir Gevorgyan

  DOI：10.1021/ol102447s

  日期：2010.12.3

  An efficient palladium-catalyzed intramolecular carbopalladation/cyclization cascade toward tetra- and pentacyclic N-fused heterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with internal propargylic esters or ethers followed by the 5-endo-dig cyclization leading to polycyclic pyrroloheterocycles in moderate to excellent yields.