12-phenyl-6H-chromeno[3,4-a]indolizin-6-one | 1268825-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 12-phenyl-6H-chromeno[3,4-a]indolizin-6-one
• 英文别名: 12-Phenylchromeno[3,4-a]indolizin-6-one；12-phenylchromeno[3,4-a]indolizin-6-one
• CAS: 1268825-47-3
• 化学式: C₂₁H₁₃NO₂
• 分子量: 311.34
• InChiKey: VXRZWHOPVVSBMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  ethyl [1,2,3]triazolo[1,5-a]pyridine-3-carboxylate 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴化亚铜二甲硫醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 12-phenyl-6H-chromeno[3,4-a]indolizin-6-one
  参考文献：
  名称：

  铜催化的吡啶并三唑的环转移反应：熔融多环吲哚嗪的普遍使用

  摘要：

  已开发了带有内部链烯基的吡咯并三唑与多种熔融多聚吲哚嗪有效的分子内跨膜反应。第一次显示它是附加的...

  DOI：

  10.1039/c5cc07598j

文献信息

• 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。
• A One-Pot Domino Reaction for the Synthesis of 3-Arylindolizines from Pyridines, Benzyl Halides, and Dihalide-Substituted Electron-Deficient Alkenes
  作者：Huayou Hu、Kunbo Shi、Rongrong Hou、Zaichao Zhang、Yulan Zhu、Jianfeng Zhou

  DOI：10.1055/s-0030-1258266

  日期：2010.12

  3-Arylindolizines were prepared by one-pot domino reactions from benzyl halides with pyridine (or isoquinoline) and cyclic or acyclic dihalide-substituted electron-deficient alkenes in the presence of potassium carbonate via in situ generated N-ylide intermediate. Both electron-donating and electron-withdrawing groups are tolerated in the aryl ring of benzyl halides. The yields range from moderate to high.

  通过一锅多米诺反应，从苄基卤化物与吡啶（或异喹啉）以及含环状或非环状二卤代取代的缺电子烯烃在碳酸钾存在下，利用原位生成的N-叶立德中间体，制备了3-芳基吲哚啉类化合物。苄基卤化物的芳环上可耐受供电子基团和吸电子基团。产率从中等到高不等。
• 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。
• Cu-catalyzed transannulation reaction of pyridotriazoles: general access to fused polycyclic indolizines
  作者：Yi Shi、Vladimir Gevorgyan

  DOI：10.1039/c5cc07598j

  日期：——

  AN EFFICIENT INTRAMOLECULAR TRANSANNULATION REACTION OF PYRIDOTRIAZOLES WITH INTERNAL ALKYNES EN ROUTE TO VARIOUS FUSED POLYCYCLIC INDOLIZINES HAS BEEN DEVELOPED. FOR THE FIRST TIME IT WAS SHOWN THAT IN ADDITION...

  已开发了带有内部链烯基的吡咯并三唑与多种熔融多聚吲哚嗪有效的分子内跨膜反应。第一次显示它是附加的...