(3,4-dichlorophenyl)(indolizin-3-yl)methanone | 675139-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4-dichlorophenyl)(indolizin-3-yl)methanone
• 英文别名: (3, 4-dichloro-phenyl)-indolizin-3-yl-methanone；Methanone, (3,4-dichlorophenyl)-3-indolizinyl-；(3,4-dichlorophenyl)-indolizin-3-ylmethanone
• CAS: 675139-19-2
• 化学式: C₁₅H₉Cl₂NO
• 分子量: 290.149
• InChiKey: BUVOHHNAVLJSMJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 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：
  21.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3,4-dichlorophenyl)(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90%的产率得到3-(3,4-dichlorobenzoyl)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：

  1-[2-(3,4-Dichlorophenyl)-2-oxoethyl]-2-methylpyridin-1-ium bromide 在 N,N-二甲基甲酰胺二甲基缩醛 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以24 %的产率得到2-(3,4-dichlorophenyl)indolizine
  参考文献：
  名称：

  微波辅助改进区域选择性合成 3-苯甲酰中氮茚衍生物

  摘要：

  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。

  DOI：

  10.1016/j.molstruc.2023.135561

文献信息

• 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。
• 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.
• SYNTHESIS OF INDOLIZINES
  申请人：Synta Pharmaceuticals Corporation

  公开号：EP1537105A2

  公开（公告）日：2005-06-08
• Synthesis of indolizines
  申请人：Synta Pharmaceuticals Corp.

  公开号：US20040152897A1

  公开（公告）日：2004-08-05

  Disclosed are methods of preparing substituted indolizines represented by the following formula: 1 comprising reacting a substrate represented by the following formula: 2 with either the cyclization reagent of the following formula: 3 or, a reagent prepared by reacting the compound represented the formula below with an alkylating agent: 4 The variables in the above formulas are defined herein.