4-fluoro-N-[2-(phenylethynyl)phenyl]benzamide | 1415218-69-7

• 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: 4-fluoro-N-[2-(phenylethynyl)phenyl]benzamide
• 英文别名: 4-fluoro-N-[2-(2-phenylethynyl)phenyl]benzamide
• CAS: 1415218-69-7
• 化学式: C₂₁H₁₄FNO
• 分子量: 315.347
• InChiKey: LKLDIHYBMWLVIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-fluoro-N-[2-(phenylethynyl)phenyl]benzamide 在 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 、 三叔丁基膦[双（三氟甲基）磺酰亚胺基]金（I） 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Differential Effect of 4H-Benzo[d] [1, 3]oxazines on the Proliferation of Breast Cancer Cell Lines

  摘要：

  Background: A family of 4H-benzo[d][1,3]oxazines were obtained from a group of N-(2-alkynyl)aryl benzamides precursors via gold(I) catalysed chemoselective 6-exo-dig C-O cyclization. Method: The precursors and oxazines obtained were studied in breast cancer cell lines MCF-7, CAMA-1, HCC1954 and SKBR-3 with differential biological activity showing various degrees of inhibition with a notable effect for those that had an aryl substituted at C-2 of the molecules. 4H-benzo[d][1,3]oxazines showed an IC50 rating from 0.30 to 157.4 µM in MCF-7, 0.16 to 139 in CAMA-1, 0.09 to 93.08 in SKBR-3, and 0.51 to 157.2 in HCC1954 cells. Results: We observed that etoposide is similar to benzoxazines while taxol effect is more potent. Four cell lines responded to benzoxazines while SKBR-3 cell line responded to precursors and benzoxazines. Compounds 16, 24, 25 and 26 have the potent effect in cell proliferation inhibition in the 4 cell lines tested and correlated with oxidant activity suggesting a possible mechanism by ROS generation. Conclusion: These compounds represent possible drug candidates for the treatment of breast cancer. However, further trials are needed to elucidate its full effect on cellular and molecular features of cancer.

  DOI：

  10.2174/0109298673292365240422104456
• 作为产物：
  描述：

  对氟苯甲酸 在 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 4-fluoro-N-[2-(phenylethynyl)phenyl]benzamide
  参考文献：
  名称：

  Differential Effect of 4H-Benzo[d] [1, 3]oxazines on the Proliferation of Breast Cancer Cell Lines

  摘要：

  Background: A family of 4H-benzo[d][1,3]oxazines were obtained from a group of N-(2-alkynyl)aryl benzamides precursors via gold(I) catalysed chemoselective 6-exo-dig C-O cyclization. Method: The precursors and oxazines obtained were studied in breast cancer cell lines MCF-7, CAMA-1, HCC1954 and SKBR-3 with differential biological activity showing various degrees of inhibition with a notable effect for those that had an aryl substituted at C-2 of the molecules. 4H-benzo[d][1,3]oxazines showed an IC50 rating from 0.30 to 157.4 µM in MCF-7, 0.16 to 139 in CAMA-1, 0.09 to 93.08 in SKBR-3, and 0.51 to 157.2 in HCC1954 cells. Results: We observed that etoposide is similar to benzoxazines while taxol effect is more potent. Four cell lines responded to benzoxazines while SKBR-3 cell line responded to precursors and benzoxazines. Compounds 16, 24, 25 and 26 have the potent effect in cell proliferation inhibition in the 4 cell lines tested and correlated with oxidant activity suggesting a possible mechanism by ROS generation. Conclusion: These compounds represent possible drug candidates for the treatment of breast cancer. However, further trials are needed to elucidate its full effect on cellular and molecular features of cancer.

  DOI：

  10.2174/0109298673292365240422104456

文献信息

• Iodine-Catalyzed, Stereo- and Regioselective Synthesis of 4-Arylidine-4H-benzo[d][1,3]oxazines and their Applications for the Synthesis of Quinazoline 3-Oxides
  作者：Wen-Chun Lee、Ho-Chuan Shen、Wan-Ping Hu、Wei-Sheng Lo、Chebrolu Murali、Jaya Kishore Vandavasi、Jeh-Jeng Wang

  DOI：10.1002/adsc.201200018

  日期：2012.8.13

  4-Benzylidene-2-aryl-4H-benzo[d][1,3] oxazines have been synthesized with high stereoselectivity and regioselectivities from 2-alkynylbenzamides in the presence of a catalytic amount of I2. In the reaction mechanism, iodine plays a key role in two different aspects as a catalyst, such as to activate the alkyne with the iodinium donor which triggers the cascade, and then as a proper acid source to facilitate

  在催化量的I 2存在下，由2-炔基苯甲酰胺以高的立体选择性和区域选择性合成了4-苄基-2-芳基-4 H-苯并[ d ] [1,3]恶嗪。在反应机理中，碘在两个不同方面起着催化剂的关键作用，例如用引发级联反应的碘供体活化炔烃，然后作为适当的酸源以促进催化剂的回收。苯并恶嗪已经被用作直接一步合成喹唑啉3-氧化物衍生物的潜在底物。
• ortho-Amide-Directed Oxidation of Internal Aryl Alkynes Mediated by Cerium(IV) Ammonium Nitrate
  作者：Jeh-Jeng Wang、Chieh-Fu Su、Wan-Ping Hu、Jaya Vandavasi、Chao-Cheng Liao、Chen-Ya Hung

  DOI：10.1055/s-0031-1290434

  日期：2012.9

  A fascinating oxidation of alkynes mediated by CAN directed by the amide group to synthesize N-[2-(2-oxo-2-phenylacetyl)phenyl]benzamide derivatives under mild conditions is reported. Excellent yields were obtained with various substituents by this method.

  据报道，在温和条件下，由酰胺基团引导的 CAN 介导的炔烃氧化合成 N-[2-(2-氧代-2-苯乙酰基)苯基]苯甲酰胺衍生物。通过该方法使用各种取代基获得了优异的产率。
• A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one
  作者：Jaya Kishore Vandavasi、Kung-Kai Kuo、Wan-Ping Hu、Ho-Chanu Shen、Wei-Sheng Lo、Jeh-Jeng Wang

  DOI：10.1039/c3ob41272e

  日期：——

  An efficient regio-, stereo- and chemo-specific synthesis of 1,3-benzoxazines via 6-exo-dig cyclization to afford the Z-isomer is reported. The structure and connectivity were confirmed unambiguously on the basis of 1H NMR, NOESY, and ORTEP. Furthermore, DFT studies revealed that the Z-isomer was more stable than the E-isomer. Iodine substituted 1,3-benzoxazines were very useful precursors for cross coupling reactions. Suzuki reaction was carried out successfully and the resulting product was transformed to 1-(4-nitrobenzoyl)-2,2-diphenylindolin-3-one in the presence of a Lewis acid.

  据报道，通过 6-exo-dig 环化可有效合成 1,3-苯并恶嗪，得到 Z-异构体。结构和连接性在 1H NMR、NOESY 和 ORTEP 的基础上得到明确证实。此外，DFT 研究表明 Z 异构体比 E 异构体更稳定。碘取代的1,3-苯并恶嗪是用于交叉偶联反应的非常有用的前体。 Suzuki反应成功进行，所得产物在路易斯酸存在下转化为1-(4-硝基苯甲酰基)-2,2-二苯基二氢吲哚-3-酮。
• F‐Tag Induced Acyl Shift in the Photochemical Cyclization of <i>o</i> ‐Alkynylated <i>N</i> ‐Alkyl‐ <i>N</i> ‐acylamides to Indoles**
  作者：Helena Simek Tosino、André Jung、Olaf Fuhr、Claudia Muhle‐Goll、Nicole Jung、Stefan Bräse

  DOI：10.1002/ejoc.202201132

  日期：2023.3.14

  3-Acylindoles with different substituents in positions N-1 and C-2 were successfully synthesized by cyclization of o-substituted N-alkyl-N-acylamides by photochemically induced 1,3-acyl shift.

  在 N-1 和 C-2 位具有不同取代基的 3-酰基吲哚通过光化学诱导的 1,3-酰基转移使邻位取代的N-烷基-N-酰基酰胺环化成功合成。
• Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles
  作者：Dattatri、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1002/adsc.202301367

  日期：2025.2.4

  We report herein a palladium‐catalyzed, site‐selective cyclative annulation of o‐alkynyl arylamides with maleimide for the stereoselective construction of succinimide‐fused benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, and downstream transformations. Control and labeling experiments were conducted to get insights into the mechanism.