butyl 3-phenylindolizine-1-carboxylate | 1394827-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: butyl 3-phenylindolizine-1-carboxylate
• CAS: 1394827-53-2
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: HNVKPMPIEKSYIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴甲苯 在 2,2,6,6-四甲基哌啶氧化物 、 caesium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 butyl 3-phenylindolizine-1-carboxylate
  参考文献：
  名称：

  伯卤代烃在合成3-芳基和3-烷基吲哚嗪中的应用

  摘要：

  吲哚利嗪是一种重要的杂环化合物，具有多种令人感兴趣的特性，使其适用于生物学，医学和材料等许多领域的众多应用。然而，尚未报道由庞大的伯卤代烷烃合成3-烷基吲哚嗪。在此，首次报道了利用串联反应从缺电子的烯烃，吡啶和伯卤代烃生成无过渡金属的3-芳基和3-烷基吲哚并嗪的合成路线。该方法的关键步骤是四氢吲哚嗪中间体与2,2,6,6-四甲基哌啶-N的氧化脱氢芳构化-氧基（TEMPO）作为氧化剂。该协议的优势在于它使用易于获得的低成本起始材料，无过渡金属的条件及其可扩展性。

  DOI：

  10.1039/c7ob00980a

文献信息

• Pd-Catalyzed C-3 functionalization of indolizines via C–H bond cleavage
  作者：Baoli Zhao

  DOI：10.1039/c2ob25643f

  日期：——

  New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C–H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc)2 catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorine substituents are tolerated. In addition, the indolizines display similar reactivities in the Pd-catalyzed reaction with 3-phenylpropiolic acid to afford the corresponding C-3 alkynylated indolizines. These methods allow the direct functionalization of indolizines in one step.

  开发了新的过渡金属催化方法，通过直接断裂C-H键实现吲哚并环己烯的芳基化。一系列芳基三氟硼酸盐在Pd(OAc)2催化剂和AgOAc氧化剂的存在下与吲哚并环己烯反应，高效地得到芳基化的吲哚并环己烯。供电子和吸电子基团均表现良好，而溴和氯取代基也可耐受。此外，吲哚并环己烯在Pd催化反应中与3-苯基丙炔酸显示出相似的反应活性，从而获得相应的C-3炔基化吲哚并环己烯。这些方法使得吲哚并环己烯能够在一步中直接进行官能团化。
• Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines
  作者：Lisheng He、Yuzhu Yang、Xiaolan Liu、Guangyan Liang、Chunyan Li、Daoping Wang、Weidong Pan

  DOI：10.1055/s-0039-1690229

  日期：2020.2

  An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction conditions. Plausible mechanisms have been proposed to explain the selective syntheses of indolizines. This protocol can be also applied to the stepwise

  已经开发出碘介导的2-（吡啶-2-基）乙酸酯衍生物与不同炔烃之间的碘介导的氧化环化反应，该反应在修饰的反应条件下提供了多重取代的吲哚嗪的区域选择性和化学选择性合成。已经提出了合理的机制来解释吲哚嗪的选择性合成。该方案也可以应用于2,2'-联吲哚并逐步合成。
• Metal-free synthesis of indolizines through oxidative C C and C N bond formations of C (sp 3 ) H bonds
  作者：N. Naresh Kumar Reddy、Darapaneni Chandra Mohan、Subbarayappa Adimurthy

  DOI：10.1016/j.tetlet.2016.01.082

  日期：2016.3

  catalyzed synthesis of indolizine-1-carboxylates through oxidative CC and CN bond formations by the reaction of 2-pyridyl acetates with alkynes and alkenes without metal, oxidant, and base. This procedure is compatible with a broad range of functional groups in both alkynes and alkenes with good yields. The reaction proceeds through a tandem CC bond formation followed by an intramolecular cyclization

  碘催化乙酸2-吡啶酯与炔烃和没有金属，氧化剂和碱的烯烃的反应，通过氧化C C和C N键的形成，催化碘吲哚-1-羧酸酯的合成。该方法与炔烃和烯烃中的多种官能团相容，且收率良好。该反应通过串联C C键的形成进行，随后进行分子内环化。
• Palladium catalyzed oxidative Suzuki coupling reaction of indolizine at the 3-position using oxygen gas as the only oxidant
  作者：Huayou Hu、Yong Liu、Juan Xu、Yuhe Kan、Chao Wang、Min Ji

  DOI：10.1039/c4ra03799e

  日期：——

  Stoichiometric metal oxidant applied in the functionalization of indolizine at the 3-position through C–H activation in a previous report was found to increase the cost of the synthesis and worsen the environmental pollution. In this paper, we developed a Pd(OAc)2/O2 catalytic system with or without ligands for an oxidative Suzuki coupling reaction of indolizine at the 3-position through C–H activation. As reported in the literature, some indolizines dimerized when catalyzed by palladium acetate under ligand-free conditions. However, we found that the dimerization of 2,3-unsubstituted indolizines was inhibited by the addition of ligands. Based on this finding, the arylation of these indolizines can be successfully achieved via a Pd(OAc)/O2 system using picolinic acid as a ligand. 1,2-disubstituted indolizines that do not easily dimerize can react smoothly with arylboronic acids under ligand-free conditions. Furthermore, broad group tolerance was shown in both indolizine and arylboronic acid. Finally, this method has the advantages of mild conditions, a broad array of starting materials and the use of a green oxidant.

  之前的报告发现，在通过 C-H 活化对吲哚利嗪进行 3 位官能化反应时，使用的化学计量金属氧化剂会增加合成成本并加剧环境污染。本文开发了一种含配体或不含配体的 Pd(OAc)2/O2 催化体系，用于通过 C-H 活化进行吲哚利嗪 3 位的氧化铃木偶联反应。据文献报道，在无配体条件下，一些吲嗪类化合物在醋酸钯催化下会发生二聚反应。然而，我们发现加入配体后，2,3-未取代的吲嗪类化合物的二聚化受到了抑制。基于这一发现，我们可以使用吡啶甲酸作为配体，通过 Pd(OAc)/O2 系统成功实现这些吲嗪类化合物的芳基化。在无配体条件下，不易发生二聚化的 1,2-二取代吲嗪类化合物能与芳基硼酸顺利发生反应。此外，吲哚利嗪和芳基硼酸都具有广泛的基团耐受性。最后，该方法还具有条件温和、起始材料广泛和使用绿色氧化剂等优点。
• Application of primary halogenated hydrocarbons for the synthesis of 3-aryl and 3-alkyl indolizines
  作者：Yan Liu、Huayou Hu、Junyu Zhou、Wenhui Wang、Youliang He、Chao Wang

  DOI：10.1039/c7ob00980a

  日期：——

  properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-aryl and 3-alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported

  吲哚利嗪是一种重要的杂环化合物，具有多种令人感兴趣的特性，使其适用于生物学，医学和材料等许多领域的众多应用。然而，尚未报道由庞大的伯卤代烷烃合成3-烷基吲哚嗪。在此，首次报道了利用串联反应从缺电子的烯烃，吡啶和伯卤代烃生成无过渡金属的3-芳基和3-烷基吲哚并嗪的合成路线。该方法的关键步骤是四氢吲哚嗪中间体与2,2,6,6-四甲基哌啶-N的氧化脱氢芳构化-氧基（TEMPO）作为氧化剂。该协议的优势在于它使用易于获得的低成本起始材料，无过渡金属的条件及其可扩展性。