3-benzoylindolizine-1-carbonitrile | 25627-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoylindolizine-1-carbonitrile
• 英文别名: 3-Benzoyl-1-cyano-indolizine
• CAS: 25627-81-0
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: ZTLNVTLAMWXXFF-UHFFFAOYSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吡啶 在 potassium dichromate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-benzoylindolizine-1-carbonitrile
  参考文献：
  名称：

  One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K₂Cr₂O₇ as an efficient oxidant under base free conditions

  摘要：

  X = 氯或溴；EWG1，EWG2 = 电子吸引基团，一锅法反应，29个例子，产率从中等到高，克级放大潜力得到确认。

  DOI：

  10.1039/c5ra06019b

文献信息

• Substituted 1-benzoyl-3-cyano-pyrrolo [1,2-a] quinolines and analogs as activators of caspases and inducers of apoptosis
  申请人：Cai Xiong Sui

  公开号：US20050014759A1

  公开（公告）日：2005-01-20

  The present invention is directed to substituted 1-benzoyl-3-cyano-pyrrolo[1,2-a]quinolines and analogs thereof, represented by the general Formula I: wherein R 1 —R 8 , L, Q, dash line and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的1-苯甲酰基-3-氰基-吡咯并[1,2-a]喹啉及其类似物，由通用式I表示： 其中R1-R8，L，Q，虚线和Ar在此定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。
• Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient­ Alkenes via One-Pot Reaction Using TEMPO as an Oxidant
  作者：Yu Zhang、Huayou Hu、Fei Shi、Zhaole Lu、Xiaolei Zhu、Weiqiu Kan、Xiang Wang

  DOI：10.1055/s-0035-1560973

  日期：——

  Abstract A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions. A one-pot method

  摘要 报道了一种由一锅法从α-卤代羰基化合物，吡啶和缺电子的烯烃合成多取代的吲哚嗪的方法。氧化脱氢反应是在使用TEMPO作为氧化剂的无过渡金属条件下进行的。该方案在温和的反应条件下，以方便的程序使用现成的起始原料。 报道了一种由一锅法从α-卤代羰基化合物，吡啶和缺电子的烯烃合成多取代的吲哚嗪的方法。氧化脱氢反应是在使用TEMPO作为氧化剂的无过渡金属条件下进行的。该方案在温和的反应条件下，以方便的程序使用现成的起始原料。
• A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives
  作者：Qun Cai、Yan-Ping Zhu、Yang Gao、Jing-Jing Sun、An-Xin Wu

  DOI：10.1139/cjc-2012-0534

  日期：2013.6

  A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylide synthesis, and 1,3-dipolar cycloaddition. The protocols were found to be highly efficient in terms of high yields, operational simplicity, mild reaction conditions, and easy workup. This method has provided an important supplement for the synthesis of indolizine derivatives via a novel tandem synthesis.

  已提出一种简洁高效的策略，可从易得的芳基或杂环芳基甲基酮、吡啶和丙烯腈合成吲哚啉衍生物。机理途径涉及碘化、吡啶铵叶立德合成和1,3-二极环加成的整合。该方案在高产率、操作简便、温和反应条件和易于操作等方面表现出高效性。这种方法为通过新颖串联合成合成吲哚啉衍生物提供了重要补充。
• Iodine-mediated one-pot synthesis of C-3 acylated indolizines from pyridines, aryl methyl ketones and acrylate derivatives
  作者：Youlai Fang、Lisheng He、Weidong Pan、Yuzhu Yang

  DOI：10.1016/j.tet.2019.05.058

  日期：2019.7

  reaction from pyridines, aryl methyl ketones and electron deficient acrylates has been accomplished in a “one-pot” manner, which provides a straightforward and efficient access to C-3 acylated indolizines. The key intermediate of N-ylides is hypothesized to be generated in situ from pyridines and (hetero)aryl methyl ketones in the presence of iodine. This method has been applied in the synthesis of two

  由吡啶，芳基甲基酮和缺乏电子的丙烯酸酯进行的I 2 / CuI促进的多组分反应已通过“一锅法”完成，可直接有效地获得C-3酰化的吲哚嗪。假设N-基团的关键中间体是在碘存在下由吡啶和（杂）芳基甲基酮原位生成的。该方法已应用于合成具有抗惊厥和抗炎活性的两个分子。
• Visible-Light-Induced Carbo-2-pyridylation of Electron-Deficient Alkenes with Pyridinium Salts
  作者：Rong-Bin Hu、Shuai Sun、Yijin Su

  DOI：10.1002/anie.201704385

  日期：2017.8.28

  A simple and practical visible-light-induced carbo-2-pyridylation of electron-deficient alkenes with readily available N-benzoylmethylpyridinium bromides is reported. More than 40 examples are presented and proceed in greater than 80 % yield (on average) with excellent regio- and diastereoselectivities.

  据报道，用容易获得的N-苯甲酰基甲基吡啶鎓溴化物，对缺电子的烯烃进行了简单，实用的可见光诱导的Carbo-2-吡啶基化。提出了40多个实例，并以优异的区域选择性和非对映选择性进行了平均收率超过80％的研究。