6-(2-Methoxy-phenyl)-3,4-dihydro-2H-pyran | 43228-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(2-Methoxy-phenyl)-3,4-dihydro-2H-pyran
• 英文别名: 3,4-Dihydro-6-(o-methoxyphenyl)-2H-pyran；6-(2-methoxyphenyl)-3,4-dihydro-2H-pyran
• CAS: 43228-99-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: VNSNYLYCZCKIGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  325.4±41.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-碘苯甲醚 、 (3,4-二氢-2H-吡喃-6-基)二甲基硅醇 在 四丁基氟化铵 、 bis(η3-allyl-μ-chloropalladium(II)) 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以74%的产率得到6-(2-Methoxy-phenyl)-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  Mild and General Cross-Coupling of (α-Alkoxyvinyl)silanols and -silyl Hydrides

  摘要：

  [GRAPHICS](alpha-Alkoxyvinyl)silanols and (alpha-alkoxyvinyl)silyl hydrides are efficiently converted to aryl vinyl ethers by a palladium(0)-catalyzed cross-coupling reaction with aryl halides in the presence of tetrabutylammonium fluoride or hydroxide. Yields are generally high, and the reaction is compatible with a wide range of functional groups.

  DOI：

  10.1021/ol0064112

文献信息

• Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O–H and N–H Additions
  作者：Jeff P. Costello、Eric M. Ferreira

  DOI：10.1021/acs.orglett.9b03557

  日期：2019.12.20

  The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization

  阐明了铂催化的分子内加氢烷氧基化中区域选择性的空间和电子驱动因素。发现了一个分支点，该分支点将过程分为 5-exo 和 6-endo 选择性过程，并且对于两种氧杂环都可以以良好的产率获得烯醇醚。主要影响来自电子效应，其中炔烃取代基诱导炔烃极化，从而导致杂原子优先攻击更缺电子的碳。在其他情况下研究电子效应，包括加氢酰氧基化和加氢胺化，尽管没有统一观察到，但方向性的类似趋势占主导地位。
• Suzuki–Miyaura cross-coupling of α-phosphoryloxy enol ethers with arylboronic acids
  作者：Lee Pedzisa、Ian W. Vaughn、Rongson Pongdee

  DOI：10.1016/j.tetlet.2008.04.116

  日期：2008.6

  The Suzuki–Miyaura cross-coupling reaction of cyclic ketene acetal phosphates with arylboronic acids was found to be a convenient and highly efficient method for the construction of aryl vinyl ethers. A wide variety of differentially substituted electron-poor and electron-rich arylboronic acids smoothly underwent the coupling process to provide the desired dihydropyrans in moderate to excellent yields

  环状烯酮缩醛磷酸酯与芳基硼酸的Suzuki-Miyaura交叉偶联反应被发现是构建芳基乙烯基醚的一种方便而高效的方法。各种各样的差异取代的贫电子和富电子芳基硼酸顺利地进行了偶联过程，以中等至极好的收率提供了所需的二氢吡喃。
• Palladium-Catalyzed Cross-Coupling Reactions between Dihydropyranylindium Reagents and Aryl Halides. Synthesis of <i>C</i>-Aryl Glycals
  作者：Ute Lehmann、Smita Awasthi、Thomas Minehan

  DOI：10.1021/ol0345428

  日期：2003.7.1

  [reaction: see text] Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl(2)Pd(PPh(3))(2) to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium

  [反应：见正文]研究了三（二氢吡喃基）铟1和卤代芳基2之间钯（0）催化的交叉偶联反应。在1-5 mol％Cl（2）Pd（PPh（3））（2）存在的情况下，芳基碘化物和缺电子的芳基溴化物与原位生成的铟试剂有效偶联，以产生具有最小（< 10％）二聚体（4）形成。衍生自D-葡萄糖的有机铟试剂也与芳基碘化物进行交叉偶联，以产生C-芳基糖基。
• Preparation of C-arylglycals via Suzuki–Miyaura cross-coupling of dihydropyranylphosphates
  作者：Michelle R. Leidy、J. Mason Hoffman、Rongson Pongdee

  DOI：10.1016/j.tetlet.2013.10.031

  日期：2013.12

  The preparation of C-arylglycals has been accomplished by employing the Suzuki-Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) groups on the aromatic ring and affords the corresponding C-arylglycals in good to excellent yields (68-97%). Additionally, the ketene acetal phosphate derived from 6-deoxy-3,4-di-O-benzyl-L-rhamnal also couples efficiently to yield C-arylglycals in excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.