(1-methylindolizin-3-yl)(phenyl)methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-methylindolizin-3-yl)(phenyl)methanone
• 英文别名: (1-Methylindolizin-3-yl)-phenylmethanone；(1-methylindolizin-3-yl)-phenylmethanone
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: QMHKPLIZCJTXSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴-4'-氰基苯乙酮 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (1-methylindolizin-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Application of DMF–methyl sulfate adduct in the regioselective synthesis of 3-acylated indolizines

  摘要：

  A number of 3-acylated indolizines were synthesized in good to excellent yields by a newly established reaction between picolinium salts and the methylsulfate salt of A (R = Me), the adduct formed from DMF-Me2SO4 as the key reagent. The low cost, short reaction time, mild reaction condition, and easy purification of the products make this an attractive new method for the synthesis of indolizine compounds. A variety of functional groups (nitro, cyano, ester, methoxy, and halogens) were well tolerated under the reaction conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.095

文献信息

• One-Pot Two-Step Synthesis of 1-(Ethoxycarbonyl)indolizines via Pyridinium Ylides
  作者：Dominik S. Allgäuer、Herbert Mayr

  DOI：10.1002/ejoc.201300784

  日期：2013.10

  = CO2Et, COMe, SO2Me, CONH2) at ambient temperature in the presence of base to give [3 + 2]-cycloadducts by stepwise [3 + 2]-cycloaddition of the intermediate pyridinium ylides. Treatment of the crude reaction mixtures with 1 equiv. of chloranil and atmospheric oxygen in the presence of sodium hydroxide gave 1-(ethoxycarbonyl)indolizines by dehydrogenation and elimination of the acceptor group (Acc)

  吡啶盐 Py+-CH2-EWG (EWG = CO2Et, CONEt2, CN, COMe, COPh) 与迈克尔受体 Ar-CH=C(CO2Et)(Acc) (Acc = CO2Et, COMe, SO2Me, CONH2) 在室温下反应碱的存在通过中间体吡啶鎓叶立德的逐步[3 + 2]-环加成得到[3 + 2]-环加合物。用1当量处理粗反应混合物。通过脱氢和消除受体基团 (Acc)，在氢氧化钠的存在下将氯苯醌和大气中的氧气转化为 1-(乙氧基羰基) 吲哚腙。从 Py+-CH2CN 和 iPr-CH=C(CO2Et)2 也获得了良好的吲哚嗪收率，这表明该方法不限于芳香迈克尔受体。结构相关的异喹啉盐与迈克尔受体类似地反应生成吡咯并[2,1-a]异喹啉。
• CuBr-Catalyzed Aerobic Decarboxylative Cycloaddition for the Synthesis of Indolizines under Solvent-Free Conditions
  作者：Wenhui Wang、Junwen Han、Jinwei Sun、Yun Liu

  DOI：10.1021/acs.joc.6b02455

  日期：2017.3.17

  An efficient synthesis of diversified indolizine derivatives was developed via CuBr-catalyzed reaction of pyridines, methyl ketones and alkenoic acids under solvent-free conditions in oxygen atmosphere. This synthesis involves cascade processes of copper-catalyzed bromination of the methyl ketone, 1,3-dipolar cycloaddition of the pyridinium ylide with the alkenoic acid, followed by oxidative decarboxylation

  通过在无溶剂条件下于氧气气氛中通过CuBr催化吡啶，甲基酮和链烯酸的反应，开发了多种吲哚嗪衍生物的有效合成方法。该合成涉及级联过程，该过程包括铜催化的甲基酮的溴化，吡啶鎓内鎓盐与链烯酸的1,3-偶极环加成反应，然后是初级环加合物的氧化脱羧和脱氢芳构化。通过该协议，可以在一锅中从简单底物中选择性地制备出具有不同取代模式的多种吲哚尼酮，并获得了良好或优异的收率。
• Iodine-Promoted Synthesis of 1-Alkyl-3-aroylindolizines from<i>N</i>-(Aroylmethyl)pyridinium Salts and Aliphatic Aldehydes
  作者：Chen Tan、Peiyun Yan、Weijian Ye、Juan Yao、Weiming Wu、Cunde Wang

  DOI：10.1002/hc.21137

  日期：2014.1

  An effective and practical method has been developed for the diversity-oriented synthesis of 1-alkyl-3-aroylindolizines via the 1,3-dipolar cycloaddition of pyridinium ylides and aliphatic aldehydes in the presence of molecular iodine and a catalytic amount of MnO2. The synthesis proceeds by tandem reactions involving [3+2] cycloaddition, dehydration of the cycloadduct, and dehydroaromatization. Molecular

  在分子碘和催化量的 MnO2 存在下，通过吡啶鎓叶立德和脂肪醛的 1,3-偶极环加成反应，开发了一种有效且实用的方法，用于多样化导向合成 1-烷基-3-芳基茚茚。该合成通过涉及 [3+2] 环加成、环加合物脱水和脱氢芳构化的串联反应进行。分子碘在反应中作为催化剂和脱氢芳构化试剂。
• Application of DMF–methyl sulfate adduct in the regioselective synthesis of 3-acylated indolizines
  作者：Teresa Przewloka、Shoujun Chen、Zhiqiang Xia、Hao Li、Shijie Zhang、Dinesh Chimmanamada、Elena Kostik、David James、Keizo Koya、Lijun Sun

  DOI：10.1016/j.tetlet.2007.06.095

  日期：2007.8

  A number of 3-acylated indolizines were synthesized in good to excellent yields by a newly established reaction between picolinium salts and the methylsulfate salt of A (R = Me), the adduct formed from DMF-Me2SO4 as the key reagent. The low cost, short reaction time, mild reaction condition, and easy purification of the products make this an attractive new method for the synthesis of indolizine compounds. A variety of functional groups (nitro, cyano, ester, methoxy, and halogens) were well tolerated under the reaction conditions. (c) 2007 Elsevier Ltd. All rights reserved.