tert-butyl 3-(3-phenylprop-2-ynyl)-1H-indole-1-carboxylate | 1234580-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 3-(3-phenylprop-2-ynyl)-1H-indole-1-carboxylate
• 英文别名: tert-butyl 3-(3-phenylprop-2-yn-1-yl)-1H-indole-1-carboxylate
• CAS: 1234580-69-8
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: XWESXVBZXVDCTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以93%的产率得到tert-butyl 3-(3-phenylprop-2-ynyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Decarboxylative Benzylations of Alkynes and Ketones

  摘要：

  Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.

  DOI：

  10.1021/ja1035557

文献信息

• Regioselective Pd-Catalyzed Carbopalladation/Decarboxylative Allylic Alkynylation of <i>ortho</i>-Iodoallenamides with Alkynyl Carboxylic Acids
  作者：Jonathan Hédouin、Vincent Carpentier、Romain M. Q. Renard、Cédric Schneider、Isabelle Gillaizeau、Christophe Hoarau

  DOI：10.1021/acs.joc.9b01408

  日期：2019.8.16

  A regioselective Pd-catalyzed domino carbopalladation/decarboxylative allylic alkynylation of ortho-iodoallenamides with alkynyl carboxylic acids was studied. This domino process, based on the consecutive formation of C(sp2)–C(sp2) and C(sp3)–C(sp) bonds, was originally achieved for the design of a novel library of prop-2-ynyl isoquinolinones and then extended to indoles. Finally, a general three-step

  研究了邻碘亚烯酰胺与炔基羧酸的区域选择性Pd催化的多米诺骨碳环化/脱羧化烯丙基炔化。这种多米诺骨牌工艺是基于连续形成C（sp 2）–C（sp 2）和C（sp 3）–C（sp）键的，最初是为了设计新型的-2-丙炔基图书馆而实现的。异喹啉酮，然后扩展到吲哚。最后，建立了一般的三步一锅策略，包括原位生成烯丙酰胺，形成π-烯丙基-Pd络合物和脱羧化烯丙基炔基。