ethyl 3-(4-fluorobenzoyl)indolizine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(4-fluorobenzoyl)indolizine-1-carboxylate
• 英文别名: Ethyl 3-(4-fluorobenzoyl)indolizine-1-carboxylate
• 化学式: C₁₈H₁₄FNO₃
• 分子量: 311.312
• InChiKey: APKHDKCSQHWHBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-氟苯基)-2-丙炔-1-醇 在 manganese(IV) oxide 、 氧气 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 ethyl 3-(4-fluorobenzoyl)indolizine-1-carboxylate
  参考文献：
  名称：

  Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

  摘要：

  A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

  DOI：

  10.1021/acs.joc.8b02883

文献信息

• Greener synthesis of indolizine analogues using water as a base and solvent: study for larvicidal activity against<i>Anopheles arabiensis</i>
  作者：Chandrashekharappa Sandeep、Katharigatta N. Venugopala、Raquel M. Gleiser、Abeen Chetram、Basavaraj Padmashali、Rashmi S. Kulkarni、Rashmi Venugopala、Bharti Odhav

  DOI：10.1111/cbdd.12823

  日期：2016.12

  Greener synthesis of a series of novel indolizine analogues have been achieved by the cyclization of aromatic cycloimmoniumylides with electron deficient alkynes in presence of water as the base and solvent at 80 degrees C. Yield of the title compounds was good and reactions performed were eco-friendly. The structures of these newly synthesized compounds have been confirmed by spectroscopic techniques

  通过在水为基础和溶剂存在下于80摄氏度下用缺电子炔烃将芳族环亚铵盐环化，可以实现一系列新型吲哚嗪类似物的绿色合成。标题化合物的收率良好，反应生态友好。这些新合成的化合物的结构已通过光谱技术（例如FTIR，NMR，LC-MS和元素分析）进行了确认。通过标准的WHO杀幼虫试验，以4杯/毫升的Temephos作为标准品，评估了表征的标题化合物对阿拉伯按蚊的杀幼虫活性。标题化合物2e，2f和2g作为有前途的杀幼虫剂出现。本文受版权保护。版权所有。
• Anti-tubercular activity and molecular docking studies of indolizine derivatives targeting mycobacterial InhA enzyme
  作者：Katharigatta N. Venugopala、Sandeep Chandrashekharappa、Pran Kishore Deb、Christophe Tratrat、Melendhran Pillay、Deepak Chopra、Nizar A. Al-Shar’i、Wafa Hourani、Lina A. Dahabiyeh、Pobitra Borah、Rahul D. Nagdeve、Susanta K. Nayak、Basavaraj Padmashali、Mohamed A. Morsy、Bandar E. Aldhubiab、Mahesh Attimarad、Anroop B. Nair、Nagaraja Sreeharsha、Michelyne Haroun、Sheena Shashikanth、Viresh Mohanlall、Raghuprasad Mailavaram

  DOI：10.1080/14756366.2021.1919889

  日期：2021.1.1

  = 16–64 µg/mL). In silico docking study revealed the enoyl-acyl carrier protein reductase (InhA) and anthranilate phosphoribosyltransferase as potential molecular targets for the indolizines. The X-ray diffraction analysis of the compound 4b was also carried out. Further, a safety study (in silico and in vitro) demonstrated no toxicity for these compounds. Thus, the indolizines warrant further development

  摘要 筛选了一系列 1,2,3-三取代的吲哚嗪（2a-2f、3a-3d和4a-4c）对敏感 H37Rv 和耐多药 (MDR)结核分枝杆菌的体外全细胞抗结核活性(MTB) 菌株。化合物2b–2d、3a–3d和4a–4c对 H37Rv-MTB 菌株具有活性，最小抑制浓度 (MIC) 范围为 4 到 32 µg/mL，而吲哚嗪4a–4c具有乙基酯基团苯甲酰基环的 4 位也表现出抗 MDR-MTB 活性（MIC = 16–64 µg/mL）。电脑模拟对接研究表明，烯酰-酰基载体蛋白还原酶（InhA）和邻氨基苯甲酸磷酸核糖转移酶是吲哚嗪的潜在分子靶标。还进行了化合物4b的X射线衍射分析。此外，一项安全性研究（计算机和体外）证明这些化合物没有毒性。因此，indolizine 需要进一步开发，并且可能代表一类新的有前途的 InhA 抑制剂和多靶向药物，以对抗药物敏感和耐药的 MTB 菌株。
• Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines
  作者：Lisheng He、Yuzhu Yang、Xiaolan Liu、Guangyan Liang、Chunyan Li、Daoping Wang、Weidong Pan

  DOI：10.1055/s-0039-1690229

  日期：2020.2

  An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction conditions. Plausible mechanisms have been proposed to explain the selective syntheses of indolizines. This protocol can be also applied to the stepwise

  已经开发出碘介导的2-（吡啶-2-基）乙酸酯衍生物与不同炔烃之间的碘介导的氧化环化反应，该反应在修饰的反应条件下提供了多重取代的吲哚嗪的区域选择性和化学选择性合成。已经提出了合理的机制来解释吲哚嗪的选择性合成。该方案也可以应用于2,2'-联吲哚并逐步合成。
• A novel approach to 3-acylated indolizine structures via iodine-mediated hydrative cyclization
  作者：Ikyon Kim、Sun Gi Kim、Ji Young Kim、Ge Hyeong Lee

  DOI：10.1016/j.tetlet.2007.10.101

  日期：2007.12

  We have discovered a new route to 3-acylated indolizine structures via iodine-mediated hydrative cyclization. Reaction mechanism is proposed for this novel transformation, which involves a 5-exo-dig iodocyclization, deprotonation, incorporation of another iodo group, deprotonation, and subsequent replacement of the diiodo group by H2O. Various 3-acylated indolizine derivatives were obtained using this mild procedure in good yields. (c) 2007 Elsevier Ltd. All rights reserved.