1-(isoquinolin-1-yl)-3-phenylprop-2-yn-1-yl pivalate | 1233883-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(isoquinolin-1-yl)-3-phenylprop-2-yn-1-yl pivalate
• CAS: 1233883-22-1
• 化学式: C₂₃H₂₁NO₂
• 分子量: 343.425
• InChiKey: KICNMVOWSOVUHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2,2-dibromostyrene 、 1-(isoquinolin-1-yl)-3-phenylprop-2-yn-1-yl pivalate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(l) chloride 作用下， 以 二甲基亚砜 、 正丁醇 为溶剂， 反应 0.83h， 以76%的产率得到3-phenyl-2-(phenylethynyl)pyrrolo[2,1-a]isoquinolin-1-yl pivalate
  参考文献：
  名称：

  Base-Controlled Cu-Catalyzed Tandem Cyclization/Alkynylation for the Synthesis of Indolizines

  摘要：

  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).

  DOI：

  10.1021/acs.orglett.6b00821
• 作为产物：
  描述：

  苯乙炔 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 1.58h， 生成 1-(isoquinolin-1-yl)-3-phenylprop-2-yn-1-yl pivalate
  参考文献：
  名称：

  Base-Controlled Cu-Catalyzed Tandem Cyclization/Alkynylation for the Synthesis of Indolizines

  摘要：

  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).

  DOI：

  10.1021/acs.orglett.6b00821

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。