4-((2-methoxyphenyl)ethynyl)benzonitrile | 862604-30-6

• 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-((2-methoxyphenyl)ethynyl)benzonitrile
• 英文别名: 4-[2-(2-Methoxyphenyl)ethynyl]benzonitrile；4-[2-(2-methoxyphenyl)ethynyl]benzonitrile
• CAS: 862604-30-6
• 化学式: C₁₆H₁₁NO
• 分子量: 233.269
• InChiKey: HZYOIBXASKBIFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((2-methoxyphenyl)ethynyl)benzonitrile 、 1-methyl-4-{[(trifluoromethyl)selanyl]sulfonyl}benzene 在 iron(III) chloride 作用下， 以 甲苯 为溶剂， 以46%的产率得到4-(3-((trifluoromethyl)selanyl)benzofuran-2-yl)benzonitrile
  参考文献：
  名称：

  Se-（三氟甲基）4-甲基苯磺酸硒酸酯的酸促进选择性合成三氟甲基硒化苯并呋喃

  摘要：

  通过使用Se-（三氟甲基）4-甲基苯磺酸亚硒酸酯作为稳定且易于制备的亲电子三氟甲基硒化试剂，公开了布朗斯台德酸促进的苯并呋喃的三氟甲基硒化。以中等至良好的产率和优异的区域选择性获得了广泛的SeCF 3-取代的苯并呋喃衍生物。通过将FeCl 3用作催化剂，还实现了1-甲氧基-2-（芳基乙炔基）苯的串联环化/三氟甲基硒化过程。

  DOI：

  10.1016/j.tetlet.2020.152809
• 作为产物：
  描述：

  5-氧代-5-苯基戊腈 在 盐酸 、 双(乙腈)氯化钯(II) 、 C₁₀H₉F₃N₂O 、 potassium carbonate 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 生成 4-((2-methoxyphenyl)ethynyl)benzonitrile
  参考文献：
  名称：

  配体促进的芳基炔基炔化：药物和天然产物结构多样性的实用工具

  摘要：

  通过Ar–C（O）裂解将众多芳基酮转化为芳基亲电体，在Sonogashira型偶联中仍然是具有挑战性但非常理想的转化。在本文中，我们报道了钯催化的配体促进的未应变芳基酮的炔基化反应。该协议允许炔基化反应以一锅法进行，具有宽泛的官能团耐受性和底物范围。该协议在药物发现和化学生物学中的潜在应用通过许多药物和天然产物的后期多样化进一步证明。更重要的是，可以通过酮的连续炔基化连接衍生自药物和天然产物的两个不同的生物学重要片段。与常规Sonogashira反应中的芳基卤化物不同，配体促进的ipso -Ar–C（O）炔基化作用使邻位C–H活化。

  DOI：

  10.1021/acscatal.0c05372

文献信息

• Photosensitizer-free, visible light-mediated recyclable gold-catalyzed cross-coupling of aryldiazonium salts and alkynyltrimethylsilanes
  作者：Jiajia Li、Junmin Chen、Hefeng Zhu、Mingzhong Cai

  DOI：10.1039/d3nj02853d

  日期：——

  temperature to afford diverse arylalkynes in moderate to good yields with high functional group tolerance, including aryl halides incompatible with traditional cross-coupling. This new heterogenized gold(I) catalyst could be easily recovered through a simple centrifugation process and reused at least nine times without any significant drop in its catalytic efficiency.

  通过(4-(氯甲基)苯乙基)三甲氧基硅烷与SBA - 15缩合，然后与( 2-(二苯基膦)苯基)甲醇和Me 2 SAuCl，然后用AgNTf 2处理并通过不同的物理化学技术进行表征。存在 10 mol% SBA-15-Ph 3 PAuNTf 2时，四氟硼酸芳基重氮盐和炔基三甲基硅烷的无光敏剂交叉偶联反应在蓝色 LED 照射下在乙腈中在室温下顺利进行，以中等至良好的产率提供多种芳基炔烃，具有高官能团耐受性，包括与传统交叉偶联不相容的芳基卤化物。这种新型多相金（I）催化剂可以通过简单的离心过程轻松回收，并重复使用至少九次，而催化效率不会出现任何显着下降。
• Can Polarization of Triple Bond in Tolanes Be Deduced from ¹³C NMR Shifts? Re-evaluation of Factors Affecting Regiochemistry of the Palladium-Catalyzed Hydrostannation of Alkynes
  作者：Michael Rubin、Alexander Trofimov、Vladimir Gevorgyan

  DOI：10.1021/ja051274v

  日期：2005.7.1

  Polarization of the triple bond in a series of differently substituted ortho- and para-tolanes has been studied by NMR and computational methods in order to examine if C-13 NMR data can be effectively used for the assessment of electronic polarization of a triple bond in diarylacetylenes. DFT calculations of both natural charges and NMR properties revealed that chemical shifts concur with effective charges on sp-carbon atoms in para-tolanes, whereas in ortho-analogues magnetic anisotropy complicates the analysis making C-13 NMR data inapplicable for ascribing triple bond polarization. The obtained information was used to reevaluate factors affecting the regiochemistry of the Pd-catalyzed hydrostannation of the triple bond in tolanes. Computational study on the polarization of triple bonds taken together with the experimental data on hydrostannation of various mono- and disubstituted tolanes bearing para- and ortho-substituents demonstrated that the regioselectivity of hydrostannation is governed by a combination of electronic and steric factors. In para-tolanes, the electronic effect prevails and alpha- and beta-vinylstannanes are obtained predominantly for substrates with electron-withdrawing and electron-donating groups, respectively. In the ortho-series, steric factors dominate over electronics and a-isomers are produced with high selectivity regardless of the substituents' nature. However, it was found that in disubstituted "push-pull" tolanes steric control of an ortho-group can be overruled by the very strong electronic effect of an electron-withdrawing substituent in para-position.
• Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate
  作者：Juyan Liu、Miaomiao Tian、Ankun Li、Liangshuo Ji、Di Qiu、Xia Zhao

  DOI：10.1016/j.tetlet.2020.152809

  日期：2021.3

  A Brönsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation

  通过使用Se-（三氟甲基）4-甲基苯磺酸亚硒酸酯作为稳定且易于制备的亲电子三氟甲基硒化试剂，公开了布朗斯台德酸促进的苯并呋喃的三氟甲基硒化。以中等至良好的产率和优异的区域选择性获得了广泛的SeCF 3-取代的苯并呋喃衍生物。通过将FeCl 3用作催化剂，还实现了1-甲氧基-2-（芳基乙炔基）苯的串联环化/三氟甲基硒化过程。
• Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products
  作者：Hui Xu、Biao Ma、Zunyun Fu、Han-Yuan Li、Xing Wang、Zhen-Yu Wang、Ling-Jun Li、Tai-Jin Cheng、Mingyue Zheng、Hui-Xiong Dai

  DOI：10.1021/acscatal.0c05372

  日期：2021.2.5

  electrophiles via Ar–C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol

  通过Ar–C（O）裂解将众多芳基酮转化为芳基亲电体，在Sonogashira型偶联中仍然是具有挑战性但非常理想的转化。在本文中，我们报道了钯催化的配体促进的未应变芳基酮的炔基化反应。该协议允许炔基化反应以一锅法进行，具有宽泛的官能团耐受性和底物范围。该协议在药物发现和化学生物学中的潜在应用通过许多药物和天然产物的后期多样化进一步证明。更重要的是，可以通过酮的连续炔基化连接衍生自药物和天然产物的两个不同的生物学重要片段。与常规Sonogashira反应中的芳基卤化物不同，配体促进的ipso -Ar–C（O）炔基化作用使邻位C–H活化。