Methyl 2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetate | 108260-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Methyl 2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetate
• CAS: 108260-70-4
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: UWYXPKQXWDNDQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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 2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(4-Hydroxy-3-methoxyphenyl)-2-methoxyacetic acid
  参考文献：
  名称：

  Structure–activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene

  摘要：

  The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon a-methylation and alpha-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (> 1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.035
• 作为产物：
  描述：

  甲醇 、 3-甲氧基-4-羟基扁桃酸 在 氯化亚砜 作用下， 反应 72.0h， 以26%的产率得到Methyl 2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetate
  参考文献：
  名称：

  Structure–activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene

  摘要：

  The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon a-methylation and alpha-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (> 1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.035

文献信息

• Herbicidal aryloxybenzeneacetic acid derivatives
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0206772A2

  公开（公告）日：1986-12-30

  Compounds of the formula wherein A is specified nitrogen-containing heterocycle; R is H2 halogen, CH3, OCH3 or OC2H5; Ri is C1-C3 alkyl, allyl or propargyl; R2 is X1R8 or OH; X1 is 0 or S; and R8 is an organic group; and their agriculturally suitable salts, exhibit herbicidal activity, especially for the selective control of weeds in rice. The compound may be made by a variety of synthetic routes, e.g. by reacting a haloheterocycle of formula A - Hal with an alkali metal salt of the appropriate 4-hydroxy-benzene- acetate ester.

  式中的化合物 其中 A 为指定的含氮杂环； R 是 H2 卤素、CH3、OCH3 或 OC2H5； Ri 是 C1-C3 烷基、烯丙基或丙炔基； R2 是 X1R8 或 OH； X1 是 0 或 S；以及 R8 是有机基团；以及它们在农业上适用的盐，具有除草活性，特别是在选择性控制水稻杂草方面。 该化合物可通过多种合成途径制得，例如通过式 A - Hal 的卤代杂环与碱金属反应 A - Hal 与适当的 4-羟基苯乙酸酯的碱金属盐反应。
• Structure–activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene
  作者：Giovanni Appendino、Abdellah Ech-Chahad、Alberto Minassi、Luciano De Petrocellis、Vincenzo Di Marzo

  DOI：10.1016/j.bmcl.2009.11.035

  日期：2010.1

  The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon a-methylation and alpha-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (> 1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date. (C) 2009 Elsevier Ltd. All rights reserved.