4-methyl-N-[2-(phenylethynyl)phenyl]benzamide | 1321594-83-5

• 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-methyl-N-[2-(phenylethynyl)phenyl]benzamide
• CAS: 1321594-83-5
• 化学式: C₂₂H₁₇NO
• 分子量: 311.383
• InChiKey: NGYBHPAUXWHZSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-methyl-N-[2-(phenylethynyl)phenyl]benzamide 在 ammonium cerium (IV) nitrate 、 氧气 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 28.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以85%的产率得到4-methyl-N-[2-(2-oxo-2-phenylacetyl)phenyl]benzamide
  参考文献：
  名称：

  由硝酸铈（IV）铵介导的内芳基炔烃的邻酰胺定向氧化

  摘要：

  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。

  DOI：

  10.1055/s-0031-1290434
• 作为产物：
  描述：

  2-碘苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 4-methyl-N-[2-(phenylethynyl)phenyl]benzamide
  参考文献：
  名称：

  Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles

  摘要：

  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.

  DOI：

  10.1002/adsc.202301367

文献信息

• A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C–H and N–H – alkyne coupling
  作者：Sk Ajarul、Anirban Kayet、Tanmay K. Pati、Dilip K. Maiti

  DOI：10.1039/c9cc07360d

  日期：——

  We demonstrated a highly competitive and selective C-C and N-C cross-coupled 7-, 6- and 5-annulation utilizing 2-ethynylanilides to afford functionalized 1H-benzo[b]azepin-2(5H)-ones, 2-quinolinones, and 3-acylindoles in high yield. ZnCl2 was found to be the smart catalyst for 7- and 5-annulation with 1,3-migration through C-H and N-H functionalization, respectively, whereas molecular iodine performed

  我们证明了利用2-乙炔基苯胺类化合物进行高度竞争和选择性的CC和NC交叉偶联7、6和5环化，可以提供官能化的1H-苯并[b]氮杂-2（5H）-酮，2-喹啉酮和3 -acylindoles高产。发现ZnCl2是7和5环化的智能催化剂，分别通过CH和NH官能化进行1,3-迁移，而分子碘以非常规的1,3 H位移进行CH官能化6环化。通过中间捕获，控制和标记实验研究了该机制。
• 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。
• Iron(III) Chloride/Diorganyl Diselenides Promoted Regio- and Stereoselective Cyclization of<i>ortho</i>-Alkynylanilides: Synthesis of (<i>Z</i>)-4-(chalcogen)methylenebenzoxazines
  作者：André L. Stein、Filipe N. Bilheri、Davi F. Back、Gilson Zeni

  DOI：10.1002/adsc.201300925

  日期：2014.2.10

  AbstractIntramolecular 6‐exo‐dig cyclization of ortho‐alkynylanilides has been employed in a regio‐ and stereoselective synthesis of (Z)‐4‐(chalcogen)methylenebenzoxazines. Several reaction parameters were screened for the efficient cyclization of ortho‐alkynylanilides. Among them, the reaction of ortho‐alkynylanilides (0.25 mmol) with iron(III) chloride (3.0 equiv.) and diorganyl diselenides (0.75 equiv.) in dichloromethane as solvent gave the products in acceptable to good yields. The resulting products were then subjected to a nitrogen–oxygen exchange reaction with ammonium acetate to furnish quinazoline derivatives. The one‐pot version of this cyclization, starting directly from 2‐alkynylanilines, avoiding the previous preparation of ortho‐alkynylanilides was also briefly studied.magnified image
• Synthesis of 3,1-Benzothiazines from 2-Alkenyl- and 2-Alkynylanilides and Lawesson Reagent
  作者：Kentaro Okuma、Saori Ozaki、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.3987/com-11-12180

  日期：——

  Reaction of 2-vinylacetanilide with P4S10 gave 2-vinylthioacetanilide, whereas reaction of 2-vinylacetanilide with Lawesson reagent (LR) afforded 2,4-dimethyl-4H-3,1-benzothiazine in 62% yield. Reaction of 2-alkynylanilides with LR gave 4-exomethylene-4H-3,1-benzothiazines in good yields.