3-methyl-2-(p-tolyl)benzofuran | 204908-14-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 3-methyl-2-(p-tolyl)benzofuran
• 英文别名: 3-Methyl-2-(4-methylphenyl)-1-benzofuran
• CAS: 204908-14-5
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: KVKSTPVOCRFDKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  13.14
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 、 乙腈 、 paraffin oil 为溶剂， 反应 4.0h， 以94.5 mg的产率得到3-methyl-2-(p-tolyl)benzofuran
  参考文献：
  名称：

  One-Pot Preparation of 2-Arylbenzofurans from Oximes with Diaryliodonium Triflate

  摘要：

  A variety of 2-arylbenzofurans were obtained in good yields by the O-arylation of oximes with diaryliodonium triflates, followed by the treatment with HCl in dioxane under warming conditions through the [3,3]-sigmatropic reaction. The present reaction is one-pot transition metal-free method for the preparation of various 2-arylbenzofurans from oximes, which are easily available from the reaction of alkyl aryl ketones with hydroxylamine

  DOI：

  10.3987/com-14-13071

文献信息

• Decarboxylative Suzuki–Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant
  作者：Jacob M. Quibell、Guojian Duan、Gregory J. P. Perry、Igor Larrosa

  DOI：10.1039/c9cc01817d

  日期：——

  of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.

  建立了用于脱羧铃木-宫浦型偶联的新方法。该方法使用碘或溴源作为脱羧介体和末端氧化剂，因此避免了以前需要化学计量的过渡金属盐。我们的新协议允许通过（杂）芳族羧酸与芳基硼酸的偶联来构建有价值的联芳构架。该脱羧化Suzuki反应的范围已经极大地多样化，从而允许先前不可获得的非邻位取代的芳族酸进行该转化。该方法还得益于催化剂用量低和不存在化学计量过渡金属添加剂的优点。
• Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides
  作者：François Bilodeau、Marie-Christine Brochu、Nicolas Guimond、Kris H. Thesen、Pat Forgione

  DOI：10.1021/jo9022793

  日期：2010.3.5

  A full overview of the decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides is described. This transformation employs palladium catalysts with short reaction times providing facile synthesis of aryl-substituted heteroaromatics. The effect of each reaction parameter including solvent, base, and additive employed as well as the full substrate scope of this

  描述了杂芳族羧酸和芳基卤化物之间的脱羧交叉偶联反应的完整概述。该转化采用反应时间短的钯催化剂，可轻松合成芳基取代的杂芳族化合物。报告了每个反应参数的影响，包括所用的溶剂，碱和添加剂，以及该转化的整个底物范围。还公开了机制证据，阐明了可能的反应途径。
• Decarboxylative biaryl synthesis in a continuous flow reactor
  作者：Paul P. Lange、Lukas J. Gooßen、Philip Podmore、Toby Underwood、Nunzio Sciammetta

  DOI：10.1039/c0cc05708h

  日期：——

  A practical protocol was developed that allows performing decarboxylative cross-coupling reactions in continuous flow reactors. Various biaryls were thus synthesized from aromatic carboxylic acids and aryl triflates using a Cu/Pd-catalyst system.

  开发了一种实际的方案，该方案允许在连续流反应器中进行脱羧交叉偶联反应。因此，使用Cu / Pd催化剂体系由芳族羧酸和芳基三氟甲磺酸酯合成了各种联芳基。
• Relay Rhodium(I)/Acid Catalysis for Rapid Access to Benzo‐2 <i>H</i> ‐Pyrans and Benzofurans
  作者：Huilong Zhu、Qianqian Zhou、Na Liu、Junhao Xing、Weijun Yao、Xiaowei Dou

  DOI：10.1002/adsc.202200024

  日期：2022.3.15

  Relay rhodium(I)/Brønsted acid catalysis for tandem arylation−cyclization reaction was developed. Chemodivergent syntheses of benzo-2H-pyrans and benzofurans from propargyl alcohols and ortho-hydroxylated arylboronic acids were achieved under this relay catalysis system. An ortho-hydroxy effect on changing the chemoselectivity and reactivity was observed.

  开发了用于串联芳基化-环化反应的中继铑（I）/布朗斯台德酸催化。在该中继催化体系下，实现了由炔丙基醇和邻羟基化芳基硼酸化学分散合成苯并-2 H-吡喃和苯并呋喃。观察到邻羟基对改变化学选择性和反应性的影响。
• Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds
  作者：Xi Yang、Gang Wang、Zhi-Shi Ye

  DOI：10.1039/d2sc03294e

  日期：——

  efficient palladium-catalyzed nucleomethylation of alkynes for the simultaneous construction of the heteroaromatic ring and methyl group. The 3-methylindoles, 3-methylbenzofurans and 4-methylisoquinolines were obtained in moderate to excellent yields. Notably, this methodology was employed as a key step for synthesis of a pregnane X receptor antagonist, zindoxifene, bazedoxifene and AFN-1252. The kinetic studies

  在此，我们公开了一种新颖且有效的钯催化炔烃核甲基化，用于同时构建杂芳环和甲基。3-甲基吲哚、3-甲基苯并呋喃和4-甲基异喹啉以中等至优异的产率获得。值得注意的是，该方法被用作合成孕烷 X 受体拮抗剂、津多昔芬、巴多昔芬和 AFN-1252 的关键步骤。动力学研究表明，还原消除可能是决定速率的步骤。