1-(pyridin-2-yl)prop-2-ynyl pivalate | 934399-66-3

• 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: 1-(pyridin-2-yl)prop-2-ynyl pivalate
• 英文别名: 1-Pyridin-2-ylprop-2-ynyl 2,2-dimethylpropanoate；1-pyridin-2-ylprop-2-ynyl 2,2-dimethylpropanoate
• CAS: 934399-66-3
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: ANJLVBQVBUNUCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(pyridin-2-yl)prop-2-ynyl pivalate 以 水 为溶剂， 反应 2.0h， 以97%的产率得到indolizin-1-yl pivalate
  参考文献：
  名称：

  Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines

  摘要：

  研究证明，丙炔醇衍生物的异环异构化反应仅在水的存在下就能生成吲哚利嗪类化合物。与以往在苯、乙腈或二氯甲烷等有机溶剂中使用与配体配对的铂、铜或银盐的方法相比，这是一项重大进步。

  DOI：

  10.1039/c0gc00198h
• 作为产物：
  描述：

  吡啶-2-甲醛 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-(pyridin-2-yl)prop-2-ynyl 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

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.
• Pt-Catalyzed Cyclization/1,2-Migration for the Synthesis of Indolizines, Pyrrolones, and Indolizinones
  作者：Cameron R. Smith、Eric M. Bunnelle、Allison J. Rhodes、Richmond Sarpong

  DOI：10.1021/ol0701971

  日期：2007.3.1

  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.
• Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines
  作者：Alison R. Hardin Narayan、Richmond Sarpong

  DOI：10.1039/c0gc00198h

  日期：——

  Hetero-cycloisomerization reactions of propargylic alcohol derivatives leading to indolizines have been demonstrated to proceed in the presence of water alone. This stands as a significant advance over the previous methods using Pt, Cu or Ag salts paired with ligands in organic solvents such as benzene, acetonitrile or methylene chloride.

  研究证明，丙炔醇衍生物的异环异构化反应仅在水的存在下就能生成吲哚利嗪类化合物。与以往在苯、乙腈或二氯甲烷等有机溶剂中使用与配体配对的铂、铜或银盐的方法相比，这是一项重大进步。