1-(pyridin-2-yl)hept-2-ynyl pivalate | 934399-68-5

• 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)hept-2-ynyl pivalate
• 英文别名: 1-Pyridin-2-ylhept-2-ynyl 2,2-dimethylpropanoate
• CAS: 934399-68-5
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: VRPGVCBTILEEGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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)hept-2-ynyl pivalate 以 水 为溶剂， 反应 2.0h， 生成 3-butylindolizin-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 、 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 4.5h， 生成 1-(pyridin-2-yl)hept-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

• 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 Triggered by the Oxidative Addition of Aroyl Chloride to Pd(0) Complex
  作者：Yahui Li、Wei Xiong、Zhifeng Zhang、Tongyu Xu

  DOI：10.1021/acs.joc.0c00161

  日期：2020.5.15

  An efficient synthesis of indolizine derivatives from propargylic pyridines and aroyl chlorides was developed. The 5-endo-dig cyclization was initiated by the in situ formed acylpalladium species from the facile oxidative addition of aroyl chloride to Pd(0) complex. This transformation successfully occurred in the presence of an N-nucleophilic moiety and acid chlorides, a good electrophilic partner

  从炔丙基吡啶和芳酰氯有效地合成了吲哚嗪衍生物。5-endo-dig环化反应是由就地形成的酰基铝化合物从芳酰氯向Pd（0）络合物的容易氧化加成开始的。在N-亲核基团和酰基氯（一种良好的亲电伙伴）的存在下成功进行了该转化，从而以良好至优异的产率提供了高度官能化的吲哚嗪。
• 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。
• 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 Carbonylative Cyclization/Arylation Cascade for 2-Aroylindolizine Synthesis
  作者：Zhou Li、Dmitri Chernyak、Vladimir Gevorgyan

  DOI：10.1021/ol302947r

  日期：2012.12.7

  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.