methyl 4-(3,4-dihydro-2H-pyran-6-yl)benzoate | 1041009-16-8

• 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-(3,4-dihydro-2H-pyran-6-yl)benzoate
• CAS: 1041009-16-8
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: XPCBACKAYHKLLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧甲酰苯硼酸频哪醇酯 、 phosphoric acid 5,6-dihydro-4H-pyran-2-yl ester diphenyl ester 在 四(三苯基膦)钯 、 三乙胺 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以92%的产率得到methyl 4-(3,4-dihydro-2H-pyran-6-yl)benzoate
  参考文献：
  名称：

  Preparation of C-arylglycals via Suzuki–Miyaura cross-coupling of dihydropyranylphosphates

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.10.031

文献信息

• 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。
• 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.