4-(2-methoxyethyl)-2-methylpyridine | 1309579-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(2-methoxyethyl)-2-methylpyridine
• CAS: 1309579-38-1
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: SDFBIJJUVJDBJN-UHFFFAOYSA-N

物化性质

• 沸点：
  210.6±25.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-methoxyethyl)-2-methylpyridine 在 苯硼酸酐 、 亚磷酸三苯酯 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 作用下， 生成 2-methyl-4-vinylpyridine
  参考文献：
  名称：

  Ruthenium-Catalyzed Conversion of sp³ C–O Bonds in Ethers to C–C Bonds Using Triarylboroxines

  摘要：

  Catalytic conversion of unreactive sp(3) C-O bonds in alkyl ethers to C-C bonds is described. Alkyl ethers bearing 2- or 4-pyridyl groups were coupled with triarylboroxines in the presence of a ruthenium catalyst. Triarylboroxines bearing a variety of functional groups including electron-withdrawing and -donating groups can be used for the reaction. No additional base was required for the coupling with the organoboron reagents, and base-sensitive groups can be tolerated. The reaction is considered to proceed via dehydroalkoxylation followed by addition of triarylboroxines to form C-C bonds.

  DOI：

  10.1021/ol2012007
• 作为产物：
  描述：

  2,4-二甲基吡啶 、 氯甲基甲基醚 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以31%的产率得到4-(2-methoxyethyl)-2-methylpyridine
  参考文献：
  名称：

  Ruthenium-Catalyzed Conversion of sp³ C–O Bonds in Ethers to C–C Bonds Using Triarylboroxines

  摘要：

  Catalytic conversion of unreactive sp(3) C-O bonds in alkyl ethers to C-C bonds is described. Alkyl ethers bearing 2- or 4-pyridyl groups were coupled with triarylboroxines in the presence of a ruthenium catalyst. Triarylboroxines bearing a variety of functional groups including electron-withdrawing and -donating groups can be used for the reaction. No additional base was required for the coupling with the organoboron reagents, and base-sensitive groups can be tolerated. The reaction is considered to proceed via dehydroalkoxylation followed by addition of triarylboroxines to form C-C bonds.

  DOI：

  10.1021/ol2012007

文献信息

• Ruthenium-Catalyzed Conversion of sp³ C–O Bonds in Ethers to C–C Bonds Using Triarylboroxines
  作者：Yohei Ogiwara、Takuya Kochi、Fumitoshi Kakiuchi

  DOI：10.1021/ol2012007

  日期：2011.6.17

  Catalytic conversion of unreactive sp(3) C-O bonds in alkyl ethers to C-C bonds is described. Alkyl ethers bearing 2- or 4-pyridyl groups were coupled with triarylboroxines in the presence of a ruthenium catalyst. Triarylboroxines bearing a variety of functional groups including electron-withdrawing and -donating groups can be used for the reaction. No additional base was required for the coupling with the organoboron reagents, and base-sensitive groups can be tolerated. The reaction is considered to proceed via dehydroalkoxylation followed by addition of triarylboroxines to form C-C bonds.