methyl 3-(4,6-dimethoxy-2-(methoxymethyl ether)-phenyl)propiolate | 1092835-50-1

• 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 3-(4,6-dimethoxy-2-(methoxymethyl ether)-phenyl)propiolate
• 英文别名: Methyl 3-[2,4-dimethoxy-6-(methoxymethoxy)phenyl]prop-2-ynoate
• CAS: 1092835-50-1
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: ICYCCEVTRCRBSD-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C
• 沸点：
  418.4±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-(4,6-dimethoxy-2-(methoxymethyl ether)-phenyl)propiolate 、 4-(叔丁基二甲基硅氧基)苯基硼酸 在 copper (I) acetate 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以76%的产率得到4'-hydroxy-5,7-dimethoxy-4-phenyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids

  摘要：

  In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.

  DOI：

  10.1021/ol802239n
• 作为产物：
  描述：

  、 氯甲酸甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 methyl 3-(4,6-dimethoxy-2-(methoxymethyl ether)-phenyl)propiolate
  参考文献：
  名称：

  Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids

  摘要：

  In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.

  DOI：

  10.1021/ol802239n

文献信息

• Gold-Catalyzed Ethynylation of Arenes
  作者：Teresa de Haro、Cristina Nevado

  DOI：10.1021/ja909726h

  日期：2010.2.10

  A novel gold-catalyzed ethynylation of aromatic rings with electron-deficient alkynes via gold catalyzed C-H activation of both C(sp)-H and C(sp(2))-H bonds has been developed. This transformation provides aromatic propiolates difficult to prepare by other methods, highlighting the synthetic potential of gold chemistry.

  已经开发出一种新的金催化的芳香环乙炔化，通过金催化 C(sp)-H 和 C(sp(2))-H 键的 CH 活化。这种转变提供了难以通过其他方法制备的芳香丙炔酸酯，突出了金化学的合成潜力。
• Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids
  作者：Yoshihiko Yamamoto、Naohiro Kirai

  DOI：10.1021/ol802239n

  日期：2008.12.18

  In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.