N-(3-fluoro-2-methylphenyl)benzamide | 453-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-fluoro-2-methylphenyl)benzamide
• 英文别名: N-(3-Fluor-o-tolyl)-benzamid；benzoic acid-(3-fluoro-2-methyl-anilide)；Benzoesaeure-(3-fluor-2-methyl-anilid)
• CAS: 453-78-1
• 化学式: C₁₄H₁₂FNO
• mdl: MFCD21415872
• 分子量: 229.254
• InChiKey: IHKUWHJNHRZJME-UHFFFAOYSA-N

物化性质

• 沸点：
  256.8±33.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)
• 熔点：
  158-159 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-fluoro-2-methylphenyl)benzamide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 4-fluoro-2-phenyl-1H-indole
  参考文献：
  名称：

  Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones

  摘要：

  已经开发出一种简单高效的铁催化的自由基环化方法，用于合成取代的锗吲哚[2,1-a]异喹啉-6(5H)-酮和吲哚啉-2-酮。

  DOI：

  10.1039/d1cc03907e
• 作为产物：
  描述：

  3-氟-2-甲基苯胺 生成 N-(3-fluoro-2-methylphenyl)benzamide
  参考文献：
  名称：

  Suschitzky, Journal of the Chemical Society, 1955, p. 4026

  摘要：

  DOI：

文献信息

• 139. Heterocyclic fluorine compounds. Part IV. Monofluoroindazoles
  作者：I. K. Barben、H. Suschitzky

  DOI：10.1039/jr9600000672

  日期：——
• New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer
  作者：Giuseppe La Regina、Ruoli Bai、Antonio Coluccia、Valeria Famiglini、Sveva Pelliccia、Sara Passacantilli、Carmela Mazzoccoli、Vitalba Ruggieri、Annalisa Verrico、Andrea Miele、Ludovica Monti、Marianna Nalli、Romina Alfonsi、Lucia Di Marcotullio、Alberto Gulino、Biancamaria Ricci、Alessandra Soriani、Angela Santoni、Michele Caraglia、Stefania Porto、Eleonora Da Pozzo、Claudia Martini、Andrea Brancale、Luciana Marinelli、Ettore Novellino、Stefania Vultaggio、Mario Varasi、Ciro Mercurio、Chiara Bigogno、Giulio Dondio、Ernest Hamel、Patrizia Lavia、Romano Silvestri

  DOI：10.1021/acs.jmedchem.5b00310

  日期：2015.8.13

  We designed 39 new 2-phenylindole derivatives as potential anticancer agents bearing the 3,4,5-trimethoxyphenyl moiety with a sulfur, ketone, or methylene bridging group at position 3 of the indole and with halogen or methoxy substituent(s) at positions 4-7. Compounds 33 and 44 strongly inhibited the growth of the P-glycoprotein-overexpressing multi-drug-resistant cell lines NCI/ADR-RES and Messa/Dx5. At 10 nM, 33 and 44 stimulated the cytotoxic activity of NK cells. At 20-50 nM, 33 and 44 arrested >80% of HeLa cells in the G2/M phase of the cell cycle, with stable arrest of mitotic progression. Cell cycle arrest was followed by cell death. Indoles 33, 44, and 81 showed strong inhibition of the SAG-induced Hedgehog signaling activation in NIH3T3 Shh-Light II cells with IC50 values of 19, 72, and 38 nM, respectively. Compounds of this class potently inhibited tubulin polymerization and cancer cell growth, including stimulation of natural killer cell cytotoxic activity and repression of Hedgehog-dependent cancer.
• Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-ones and indolin-2-ones
  作者：Yani Luo、Tian Tian、Yasushi Nishihara、Leiyang Lv、Zhiping Li

  DOI：10.1039/d1cc03907e

  日期：——

  A simple and efficient iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones has been developed.

  已经开发出一种简单高效的铁催化的自由基环化方法，用于合成取代的锗吲哚[2,1-a]异喹啉-6(5H)-酮和吲哚啉-2-酮。

• Suschitzky, Journal of the Chemical Society, 1955, p. 4026
  作者：Suschitzky

  DOI：——

  日期：——