3-氟-N-(4-甲氧基苯基)苯甲酰胺 | 58955-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氟-N-(4-甲氧基苯基)苯甲酰胺
• 英文名称: 3-fluoro-N-(4-methoxyphenyl)benzamide
• CAS: 58955-03-6
• 化学式: C₁₄H₁₂FNO₂
• mdl: MFCD00439072
• 分子量: 245.253
• InChiKey: QQHQVSLNPRAISI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氟-N-(4-甲氧基苯基)苯甲酰胺 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  Benzisothiazolones as modulators of macrophage migration inhibitory factor

  摘要：

  Substituted N-phenylbenzisothiazolones have been investigated as inhibitors of the tautomerase activity of the proinflammatory cytokine MIF (macrophage migration inhibitory factor). Numerous compounds were found to possess antagonist activity in the low micromolar range with the most potent being the 6-hydroxy analog 1w. Compound 1w and the p-cyano analog 1c were also shown to exhibit significant inhibition of the binding of MIF to its transmembrane receptor CD74. Consistently, both compounds were also found to retard the MIF-dependent phosphorylation of ERK1/2 in human synovial fibroblasts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.127
• 作为产物：
  描述：

  间氟苯甲酰胺 、 4-碘苯甲醚 在 copper(l) iodide 、 manganese(II) fluoride 、 反式-1,2-环己二胺 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以29%的产率得到3-氟-N-(4-甲氧基苯基)苯甲酰胺
  参考文献：
  名称：

  在水中温和条件下用于酰胺和磺酰胺 N-芳基化的高效锰/铜双金属催化剂

  摘要：

  开发了一种在 60 °C 下在水中使用双金属 MnF2/CuI 催化剂的有效且温和的方法，用于酰胺和磺酰胺与芳基卤化物的 N-芳基化。各种官能化酰胺和磺酰胺与不同的取代芳基卤化物偶联，以良好至极好的产率（高达 97%）提供相应的 N-芳基化产物。

  DOI：

  10.1002/ejoc.201201218

文献信息

• Nickel-Catalyzed Denitrogenative Cross-Coupling Reaction of 1,2,3-Benzotriazin-4(3<i>H</i>)-ones with Organoboronic Acids: An Easy Access to<i>Ortho</i>-Arylated and Alkenylated Benzamides
  作者：Madasamy Hari Balakrishnan、Kotturaja Sathriyan、Subramaniyan Mannathan

  DOI：10.1021/acs.orglett.8b01401

  日期：2018.7.6

  A novel nickel-catalyzed approach to synthesize ortho-arylated and alkenylated benzamides in good to high yields via a denitrogenative cross-coupling reaction of 1,2,3-benzotriazin-4(3H)-ones with organoboronic acids is described. The reaction proceeds through a five-membered azanickelacyclic intermediate with the extrusion of a nitrogen molecule. Moreover, the resulting ortho-arylated benzamides were

  一种新的镍催化的方法来合成邻-arylated和经由1,2,3-苯并三嗪-4（3的denitrogenative交叉偶联反应以优良至高产率链烯基苯甲酰胺ħ） -酮与有机硼酸进行说明。该反应通过五元氮杂氮杂环中间体与氮分子的挤出而进行。此外，将得到的邻芳基化的苯甲酰胺成功地以高收率转化成合成上有用的取代的芴酮和邻芳基化的苄胺衍生物。
• Synthesis and biological relationships of 3′,6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents
  作者：Ya-Yun Lai、Li-Jiau Huang、Kuo-Hsiung Lee、Zhiyan Xiao、Kenneth F. Bastow、Takao Yamori、Sheng-Chu Kuo

  DOI：10.1016/j.bmc.2004.09.041

  日期：2005.1

  decreased significantly if a chlorine or methoxy group replaced the fluorine atom. 3'-Fluoro-6-methoxy-2-phenyl-4-quinolone-3-carboxylic acid (68) had the highest in vitro cytotoxic activity among all tested carboxylic acid derivatives and their salts. The mechanism of action may be similar, but not identical, to that of tubulin binding drugs, such as navelbine and taxol. Compound 68 merits further investigation

  作为对2-苯基-4-喹诺酮系列中潜在抗癌候选药物的持续搜索的一部分，合成并评估了3'，6-取代的2-苯基-4-喹诺酮-3-羧酸衍生物及其盐。初步筛选显示，含有间氟取代的2-苯基的羧酸类似物具有最高的体外抗癌活性。如果氯或甲氧基取代氟原子，则活性会显着降低。在所有测试的羧酸衍生物及其盐中，3'-氟-6-甲氧基-2-苯基-4-喹诺酮-3-羧酸（68）的体外细胞毒性活性最高。作用机理可能与结合微管蛋白的药物（如纳韦宾和紫杉醇）相似但不相同。化合物68作为新型亲水抗有丝分裂剂值得进一步研究。
• Efficient Manganese/Copper Bimetallic Catalyst for<i>N</i>-Arylation of Amides and Sulfonamides Under Mild Conditions in Water
  作者：Yong-Chua Teo、Fui-Fong Yong、Idzham Khalid Ithnin、Siew-Hui Trionna Yio、Zhiyin Lin

  DOI：10.1002/ejoc.201201218

  日期：2013.1

  An efficient and mild method using a bimetallic MnF2/CuI catalyst at 60 °C in water was developed for the N-arylation of amides and sulfonamides with aryl halides. A variety of functionalized amides and sulfonamides were coupled with different substituted aryl halides to afford the corresponding N-arylated products in good to excellent yields (up to 97 %).

  开发了一种在 60 °C 下在水中使用双金属 MnF2/CuI 催化剂的有效且温和的方法，用于酰胺和磺酰胺与芳基卤化物的 N-芳基化。各种官能化酰胺和磺酰胺与不同的取代芳基卤化物偶联，以良好至极好的产率（高达 97%）提供相应的 N-芳基化产物。
• Benzisothiazolones as modulators of macrophage migration inhibitory factor
  作者：William L. Jorgensen、Alexander Trofimov、Xin Du、Alissa A. Hare、Lin Leng、Richard Bucala

  DOI：10.1016/j.bmcl.2011.05.127

  日期：2011.8

  Substituted N-phenylbenzisothiazolones have been investigated as inhibitors of the tautomerase activity of the proinflammatory cytokine MIF (macrophage migration inhibitory factor). Numerous compounds were found to possess antagonist activity in the low micromolar range with the most potent being the 6-hydroxy analog 1w. Compound 1w and the p-cyano analog 1c were also shown to exhibit significant inhibition of the binding of MIF to its transmembrane receptor CD74. Consistently, both compounds were also found to retard the MIF-dependent phosphorylation of ERK1/2 in human synovial fibroblasts. (C) 2011 Elsevier Ltd. All rights reserved.

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