methyl 4-[(2E)-5-hydroxy-3,7-dimethylocta-2,6-dienoxy]-3-methoxybenzoate | 212958-28-6

• 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-[(2E)-5-hydroxy-3,7-dimethylocta-2,6-dienoxy]-3-methoxybenzoate
• CAS: 212958-28-6
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: ZHHFWCDUMCDYJF-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-[(2E)-5-hydroxy-3,7-dimethylocta-2,6-dienoxy]-3-methoxybenzoate 在 pyridinium chlorochromate absorbed on neutral alumina 作用下， 以 正己烷 为溶剂， 反应 24.0h， 以30%的产率得到Methyl 4[(2e)-3,7-dimethyl-5-oxo-2,6-octadienyl]oxy-3-methoxybenzoate
  参考文献：
  名称：

  Synthesis of Geranyl Phenyl Ethers Based on the Cytotoxic Monoterpenoids from the Liverwort Genus Trichocolea

  摘要：

  The synthesis of three geranyl ethers, methyl 4-[{(2E)-3,7-dimethyl-5-oxo-2,6-octadienyl}oxy]-3-methoxybenzoate (1), methyl 4-[{(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-methoxybenzoate (2), and methyl 4-[{(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-hydroxybenzoate (3), previously isolated from New Zealand Trichocolea liverworts, is described. Differing reactivity of the hydroxy groups of methyl protocatachuate toward alkylation and the ability of alkyl groups to migrate from oxygen to an ortho-oxygen in these benzene derivatives are noted.

  DOI：

  10.1021/np980031w
• 作为产物：
  描述：

  (E)-8-chloro-2,6-dimethyl-octa-2,6-dien-4-one 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.25h， 生成 methyl 4-[(2E)-5-hydroxy-3,7-dimethylocta-2,6-dienoxy]-3-methoxybenzoate
  参考文献：
  名称：

  Synthesis of Geranyl Phenyl Ethers Based on the Cytotoxic Monoterpenoids from the Liverwort Genus Trichocolea

  摘要：

  The synthesis of three geranyl ethers, methyl 4-[{(2E)-3,7-dimethyl-5-oxo-2,6-octadienyl}oxy]-3-methoxybenzoate (1), methyl 4-[{(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-methoxybenzoate (2), and methyl 4-[{(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-hydroxybenzoate (3), previously isolated from New Zealand Trichocolea liverworts, is described. Differing reactivity of the hydroxy groups of methyl protocatachuate toward alkylation and the ability of alkyl groups to migrate from oxygen to an ortho-oxygen in these benzene derivatives are noted.

  DOI：

  10.1021/np980031w

文献信息

• Synthesis of Geranyl Phenyl Ethers Based on the Cytotoxic Monoterpenoids from the Liverwort Genus <i>Trichocolea</i>
  作者：Seung-Hwa Baek、Nigel B. Perry、Rex T. Weavers

  DOI：10.1021/np980031w

  日期：1998.9.1

  The synthesis of three geranyl ethers, methyl 4-[(2E)-3,7-dimethyl-5-oxo-2,6-octadienyl}oxy]-3-methoxybenzoate (1), methyl 4-[(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-methoxybenzoate (2), and methyl 4-[(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-hydroxybenzoate (3), previously isolated from New Zealand Trichocolea liverworts, is described. Differing reactivity of the hydroxy groups of methyl protocatachuate toward alkylation and the ability of alkyl groups to migrate from oxygen to an ortho-oxygen in these benzene derivatives are noted.