methyl 4-[(2-methoxyphenyl)ethynyl]benzoate | 229174-44-1

• 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: methyl 4-[(2-methoxyphenyl)ethynyl]benzoate
• 英文别名: Methyl 4-[2-(2-methoxyphenyl)ethynyl]benzoate
• CAS: 229174-44-1
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: DMJDXBUAQVDXFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-[(2-methoxyphenyl)ethynyl]benzoate 在 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 以97%的产率得到4-(2-methoxyphenylethynyl)benzoic acid
  参考文献：
  名称：

  分子线和器件的合成和初步测试。

  摘要：

  本文介绍了几种共轭低聚（亚苯基乙炔基）合成路线。这些低聚物中的一些不含官能团，而其他则具有供体基团，受体基团，卟啉内部以及用于各种潜在传输和数字设备应用的其他杂环内部。提出了具有各种端基的低聚（亚苯基亚乙炔基）的合成方法，该低端基用于连接许多金属探针和表面。一些功能化分子系统表现出线性，线状，电流对电压（I（V））响应，而另一些则表现出负差分电阻（NDR）和分子随机存取记忆效应的非线性I（V）曲线。最后，描述了可以在金属电极上形成自组装单分子层的功能化低聚物的合成，从而降低了肖特基势垒。肖特基势垒研究的信息可以为分子电子学中的分子鳄鱼夹优化提供有用的见解。

  DOI：

  10.1002/1521-3765(20011203)7:23<5118::aid-chem5118>3.0.co;2-1
• 作为产物：
  描述：

  2-(三甲基甲硅烷基乙炔基)苯甲醚 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 生成 methyl 4-[(2-methoxyphenyl)ethynyl]benzoate
  参考文献：
  名称：

  功能化烯烃的无CO对映选择性加氢甲酰基化：使用双重催化剂体系可提高选择性和产率

  摘要：

  研究了使用由1,2-双-（（2,5）-二苯基膦基）乙烷作为手性配体衍生的高活性单一催化剂体系进行的无一氧化碳不对称转移加氢甲酰化（ATHF）程序的范围。这揭示了一些非常成功的反应，但也有明显的局限性。描述了新方案的发展，在该方案中，将甲醛分解为CO和H 2的催化剂与随后进行不对称加氢甲酰化的选择催化剂结合使用。这使得有问题的ATHF反应得以显着改善。该新方法已用于生物活性分子的几种关键前体的合成中。

  DOI：

  10.1002/adsc.201900640

文献信息

• Low Temperature Sonogashira Coupling Reaction
  作者：Keiichi Nakamura、Hitoshi Okubo、Masahiko Yamaguchi

  DOI：10.1055/s-1999-2684

  日期：1999.5

  A low temperature Sonogashira reaction was developed, which coupled equimolar amount of aryl iodide possessing electron-withdrawing groups with aromatic acetylene at - 20 °C in quantitative yield.

  开发了一种低温Sonogashira反应，在-20°C下将带有吸电子基团的等摩尔量芳基碘与芳香乙炔以定量产率偶联。
• 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。
• Iridium-Catalyzed Intramolecular Methoxy C−H Addition to Carbon-Carbon Triple Bonds: Direct Synthesis of 3-Substituted Benzofurans from <i>o</i> -Methoxyphenylalkynes
  作者：Takeru Torigoe、Toshimichi Ohmura、Michinori Suginome

  DOI：10.1002/chem.201602152

  日期：2016.7.18

  Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C−H bond of a methoxy group in 1‐methoxy‐2‐(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p‐xylene at 135 °C in the presence of an iridium catalyst. The initial 5‐exo cyclization products underwent double‐bond migration during the

  用甲基醚完成炔烃的催化加氢烷基化。在110°C的甲苯中或在135°C的135°C的对二甲苯中，通过碳-碳三键在1-甲氧基-2-（芳基乙炔基）苯中的甲氧基C-H键分子内加成有效。铱催化剂的存在。最初的5-exo环化产物在反应过程中经历了双键迁移，从而以高收率获得了3-（芳基甲基）苯并呋喃。
• 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.
• Shen, Wang, Synlett, 2000, # 5, p. 737 - 739
  作者：Shen, Wang

  DOI：——

  日期：——