(4-chlorophenyl)(indolizin-3-yl)methanone | 675139-18-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-chlorophenyl)(indolizin-3-yl)methanone
• 英文别名: Methanone, (4-chlorophenyl)-3-indolizinyl-；(4-chlorophenyl)-indolizin-3-ylmethanone
• CAS: 675139-18-1
• 化学式: C₁₅H₁₀ClNO
• 分子量: 255.703
• InChiKey: UKOXJUYPEWYGRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)(indolizin-3-yl)methanone 、 溶剂黄146 在 碘苯二乙酸 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以88%的产率得到3-(4-chlorobenzoyl)indolizin-1-yl acetate
  参考文献：
  名称：

  Palladium-catalyzed direct and regioselective C–H acyloxylation of indolizines

  摘要：

  通过钯催化的C-H官能化，开发了一种直接且高度区域选择性的吲哚啉C1-酰氧化反应。在这个反应中，在没有引导基团的情况下实现了区域选择性。

  DOI：

  10.1039/c5ob01359c
• 作为产物：
  描述：

  马来酸酐 、 1-(2-(4-chlorophenyl)-2-oxoethyl)pyridinium bromide 在 tetrakispyridinecobalt(II) di(chromate) 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以78%的产率得到(4-chlorophenyl)(indolizin-3-yl)methanone
  参考文献：
  名称：

  通过N-内酯与马来酸酐的1,3-偶极环加成反应， 区域选择性合成3-acylindolizines和苯并类似物†

  摘要：

  3-Acylindolizines（5a-5f）和它们的苯并类似物1-acylpyrrolo [1,2- a ] quinolines（6a - 6f）和1-acylpyrrolo [2,1- a ] isoquinolines （7a-7i）是通过区域选择性合成的相应的吡啶鎓（喹啉鎓，异喹啉鎓）内酯与马来酸酐 （嘛）在弱氧化剂存在下 四铬吡啶钴（II）重铬酸盐 （TPCD）。这些反应通过偶氮甲meth内酯与1,3,3-偶极环加成的串联反应序列进行嘛， 酐 水解和一级环加合物的氧化双脱羧，然后将二氢吲哚并咪唑脱氢芳构化。 TPCD在反应中同时用作脱羧剂和脱氢剂。这些结果表明TPCD 是用于脂肪族羧酸酯双脱羧的有前途的新试剂。

  DOI：

  10.1039/c000277a

文献信息

• 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。
• TEMPO‐catalyzed decarboxylation reactions for the synthesis of 1,2‐unsubstituted indolizines
  作者：Yuxuan Zhang、Wenhui Wang、Jinwei Sun、Yun Liu

  DOI：10.1002/jhet.3766

  日期：2020.1

  An efficient synthesis of 1,2‐unsubstituted indolizines was developed via 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO)–catalyzed decarboxylation reaction. A series of target products were successfully prepared with the tolerance of a variety of functional groups. This protocol features advantages such as easily available substrates, broad substituent scope, and eco‐friendly conditions.

  通过2,2,6,6-四甲基哌啶-1-氧基（TEMPO）催化的脱羧反应，开发了1,2-未取代的吲哚嗪的有效合成方法。已成功制备了具有各种功能基团耐受性的一系列目标产品。该协议具有以下优点：容易获得的底物，广泛的取代基范围和环保条件。
• Microwave-Assisted Improved Regioselective Synthesis of 3-Benzoyl Indolizine Derivatives
  作者：Gopavaram Sumanth、Surbhi Mahender Saini、Kyatagani Lakshmikanth、Gayakvad Sunitaben Mangubhai、Kondreddy Shivaprasad、Sandeep Chandrashekharappa

  DOI：10.1016/j.molstruc.2023.135561

  日期：2023.8

  yield under microwave irradiation and the obtained yield was compared with the conventional synthesis method after column purification. Different novel 3-benzoyl indolizine derivatives were synthesized by microwave irradiation. The newly synthesized compound structures were characterized by spectral analysis such as 1H-NMR, 13C-NMR, and HRMS.

  开发了一种在微波辐射下通过双组分反应合成 3-苯甲酰中氮氢化合物的高效简便方法。底物适用范围广，在微波辐射下得到目标产物3-苯甲酰中氮，收率为74-89%，并与柱纯化后的常规合成方法进行了收率比较。通过微波辐射合成了不同的新型 3-苯甲酰中氮衍生物。通过1 H-NMR、13 C-NMR 和 HRMS 等光谱分析对新合成的化合物结构进行了表征。
• 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.
• Controlling chemoselectivity—application of DMF di-t-butyl acetal in the regioselective synthesis of 3-monosubstituted indolizines
  作者：Zhiqiang Xia、Teresa Przewloka、Keizo Koya、Mitsunori Ono、Shoujun Chen、Lijun Sun

  DOI：10.1016/j.tetlet.2006.10.052

  日期：2006.12

  Among a number of DMF dialkyl acetals investigated for the regioselective synthesis of 3-acylindolizines, the di-t-butyl acetal, via its iminium intermediate readily formed in situ, provides the highest chemoselectivity for the intermolecular cyclization of picolinium salts. DMF di-i-butyl acetal was applied to the syntheses of a variety of 3-acylated indolizines including alkyl, aryl, and heteroaryl substituents. (c) 2006 Elsevier Ltd. All rights reserved.