3-(1-cyclohexenyl)-1-(pyridin-2-yl)prop-2-ynyl pivalate | 934399-74-3

• 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: 3-(1-cyclohexenyl)-1-(pyridin-2-yl)prop-2-ynyl pivalate
• 英文别名: 3-cyclohexenyl-1-(pyridin-2-yl)prop-2-ynyl pivalate；3-(cyclohex-1-en-1-yl)-1-(pyridin-2-yl)prop-2-yn-1-yl pivalate；[3-(Cyclohexen-1-yl)-1-pyridin-2-ylprop-2-ynyl] 2,2-dimethylpropanoate
• CAS: 934399-74-3
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: LDMXGUCQPFMICD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  3-(1-cyclohexenyl)-1-(pyridin-2-yl)prop-2-ynyl pivalate 在 indium(III) chloride 作用下， 以 苯 为溶剂， 反应 2.0h， 以81%的产率得到3-(1-cyclohexenyl)indolizin-1-yl pivalate
  参考文献：
  名称：

  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.02.103
• 作为产物：
  描述：

  1-乙炔基环己烷 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 3-(1-cyclohexenyl)-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

• 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-Controlled Cu-Catalyzed Tandem Cyclization/Alkynylation for the Synthesis of Indolizines
  作者：Kyung Hwan Oh、Seong Min Kim、Sun Young Park、Jin Kyoon Park

  DOI：10.1021/acs.orglett.6b00821

  日期：2016.5.6

  A base-controlled Cu-catalyzed tandem cyclization/alkynylation of propargylic amines provides rapid access to functionalized indolizine derivatives under mild reaction conditions. The reaction first proceeded via a 5-endo-dig aminocupration, followed by a coupling between the copper bound intermediate and alkynyl bromide, to afford the products in good to excellent yields. The successful tandem reaction is attributed to the unique property of the bases, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and MTBD (7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene used).
• 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.