8a-methyl-2-(4-nitrophenyl)-3-phenylindolizin-1(8aH)-one | 1221508-84-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 8a-methyl-2-(4-nitrophenyl)-3-phenylindolizin-1(8aH)-one
• 英文别名: 8a-Methyl-2-(4-nitrophenyl)-3-phenylindolizin-1-one
• CAS: 1221508-84-4
• 化学式: C₂₁H₁₆N₂O₃
• 分子量: 344.37
• InChiKey: ZTZPMDIUPICZRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8a-methyl-2-(4-nitrophenyl)-3-phenylindolizin-1(8aH)-one 以 氯仿 、 甲苯 为溶剂， 反应 12.08h， 生成
  参考文献：
  名称：

  一类带氮的带电环嗪在外围的离域效应和可调发射

  摘要：

  提出了一种新型的环嗪类似物，其外围让人联想到aza [10]环戊烯骨架，内部被sp 3碳束缚。在基于NMR和X射线衍射数据的深度结构分析中，可以更深入地了解电子离域对其结构和性质的影响。化学位移位置的特征变化表明在这些系统中存在芳环电流。固态和溶液态中涉及电荷转移的有吸引力的发射特性是另一个亮点。

  DOI：

  10.1021/acs.orglett.1c00827
• 作为产物：
  描述：

  3-Hydroxy-3-<2>-pyridyl-but-1-in 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 13.0h， 生成 8a-methyl-2-(4-nitrophenyl)-3-phenylindolizin-1(8aH)-one
  参考文献：
  名称：

  Palladium-catalyzed construction of poly-substituted indolizinones

  摘要：

  We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elimination, and 1,2-shift. While our previous effort to the same skeleton via 2-iodoindolizinones selected alpha,beta-unsaturated esters, terminal acetylenes, or boronic acids as coupling partners, this strategy introduces new functional groups at the C2 position of indolizinone core with (hetero)aryl halides or diallyl carbonate, expanding the substrate scope for decoration at the C2 site. Furthermore, a new preparation route to tertiary propargylic alcohols for this study is described to rapidly diversify the molecular framework. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.091

文献信息

• Synthesis of new cyclazines and 4,5-diaryl-1<i>H</i>-pyrrol-3(2<i>H</i>)-one units in discoipyrroles from indolizinone-DMAD cycloadducts
  作者：Jais Kurian、Muraleedharan Kannoth M.

  DOI：10.1039/c9ob01655d

  日期：——

  access to 3',8a-dihydrocyclopenta[hi]indolizin-8a-ol and 1H-pyrrol-3(2H)-one in good yields. The former skeleton is a precursor to cyclazines with nitrogen on the periphery, a hitherto un-accessed 10-π system. Their formation involves initial [4 + 2] or [8 + 2] modes of cycloadditions; the retro-Diels Alder reaction of the [4 + 2] cycloadduct leads to 1H-pyrrol-3(2H)-one, whereas [8 + 2] addition followed

  吲哚嗪酮与乙酰二羧酸二甲酯的反应以良好的收率直接获得了3'，8a-二氢环戊基吲哚嗪-8a-ol和1H-吡咯-3（2H）-。前者的骨架是环嗪的前体，环上有氮，这是迄今尚未得到的10-π系统。它们的形成涉及初始的[4 + 2]或[8 + 2]环加成反应模式。[4 + 2]环加合物的Diels Alder逆反应生成1H-吡咯-3（2H）-1，而[8 + 2]加π重组后形成氮杂腈。取代基对产物分布的影响分析表明，C3-芳基环上的给电子基团显着促进了氮杂三环的形成。用HBF4处理这些氮杂三环化合物之一（3c）导致形成相应的10e-芳香族物质，该物质通过NMR光谱检测。此外，通过正常的逆Diels Alder途径形成1H-吡咯-3（2H）-一个骨架被用于Discooipyrrole C的全合成，这是对抗肺癌的新途径。
• Expeditious Synthesis of Highly Substituted Indolizinones via a Palladium-Catalyzed Domino Sequence
  作者：Ikyon Kim、Kyungsun Kim

  DOI：10.1021/ol1006778

  日期：2010.6.4

  A direct one-pot approach to polysubstituted indolizinones from tertiary propargylic alcohols using a palladium-catalyzed domino process involving aminopalladation, reductive elimination, and 1,2-shift is described.
• Diversity-Oriented Construction of Highly Substituted Indolizinones
  作者：Kyungsun Kim、Ikyon Kim

  DOI：10.1021/cc100015k

  日期：2010.5.10

  Rapid generation of small library of highly functionalized indolizonones was realized by exploiting three palladium-catalyzed cross-coupling reactions of 2-iodoindolizinones which in turn were readily accessed via sequential iodine-mediated cyclization/1,2-shift reactions of propargylic alcohols.
• Palladium-catalyzed construction of poly-substituted indolizinones
  作者：Hanyang Cho、Ikyon Kim

  DOI：10.1016/j.tet.2012.04.091

  日期：2012.7

  We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elimination, and 1,2-shift. While our previous effort to the same skeleton via 2-iodoindolizinones selected alpha,beta-unsaturated esters, terminal acetylenes, or boronic acids as coupling partners, this strategy introduces new functional groups at the C2 position of indolizinone core with (hetero)aryl halides or diallyl carbonate, expanding the substrate scope for decoration at the C2 site. Furthermore, a new preparation route to tertiary propargylic alcohols for this study is described to rapidly diversify the molecular framework. (c) 2012 Elsevier Ltd. All rights reserved.
• Delocalization Effects and Tunable Emission in a Class of Charged Cyclazines with Nitrogen on the Periphery
  作者：Jais Kurian、Kanneth S. Shurooque、Venkatachalam Ramkumar、Lakshmi Chakkumkumarath、Muraleedharan Kannoth M.

  DOI：10.1021/acs.orglett.1c00827

  日期：2021.5.7

  A new class of cyclazine analogues with periphery reminiscent of an aza[10]annulene framework, tethered internally by an sp3 carbon, is presented. In depth structure analysis based on NMR and X-ray diffraction data gave a deeper insight into the effect of electron delocalization on their structure and properties. A characteristic change in chemical shift positions suggested an aromatic ring current

  提出了一种新型的环嗪类似物，其外围让人联想到aza [10]环戊烯骨架，内部被sp 3碳束缚。在基于NMR和X射线衍射数据的深度结构分析中，可以更深入地了解电子离域对其结构和性质的影响。化学位移位置的特征变化表明在这些系统中存在芳环电流。固态和溶液态中涉及电荷转移的有吸引力的发射特性是另一个亮点。