methyl (3-azido-4-methoxyphenyl)acetate | 137346-00-0

• 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-azido-4-methoxyphenyl)acetate
• 英文别名: Methyl 2-(3-azido-4-methoxyphenyl)acetate
• CAS: 137346-00-0
• 化学式: C₁₀H₁₁N₃O₃
• 分子量: 221.216
• InChiKey: WENIPLOBAYCHPL-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：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3-azido-4-methoxyphenyl)acetate 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以69%的产率得到3-叠氮基-4-甲氧基苯乙酸
  参考文献：
  名称：

  Similarities and Differences in the Structure−Activity Relationships of Capsaicin and Resiniferatoxin Analogues

  摘要：

  Structure-activity relationships in analogues of the irritant natural product capsaicin have previously been rationalized by subdivision of the molecule into three structural regions (A, B, and C). The hypothesis that resiniferatoxin (RTX), which is a high-potency ligand for the same receptor and which has superficial structural similarities with capsaicin, could be analogously subdivided has been investigated. The effects of making parallel changes in the two structural series have been studied in a cellular functional assay which is predictive of analgesic activity. Parallel structural changes in the two series lead to markedly different consequences on biological activity; the 3- and 4-position aryl substituents (corresponding to the capsaicin 'A-region') which are strictly required for activity in capsaicin analogues are not important in RTX analogues. The homovanillyl C-20 ester group in RTX (corresponding to the capsaicin 'B-region') is more potent than the corresponding amide, in contrast to the capsaicin analogues. Structural variations to the diterpene moiety suggest that the functionalized 5-membered diterpene ring of RTX is an important structural determinant for high potency. Modeling studies indicate that the 3D position of the alpha-hydroxy ketone moiety in the 5-membered ring is markedly different in the phorbol (inactive) analogues and RTX (active) series. This difference appears to be due to the influence of the strained ortho ester group in RTX, which acts as a local conformational constraint. The reduced activity of an analogue substituted in this region and the inactivity of a simplified analogue in which this unit is entirely removed support this conclusion.

  DOI：

  10.1021/jm960139d
• 作为产物：
  描述：

  4-甲氧基苯乙酸甲酯 在 叠氮基三甲基硅烷 、 [双(三氟乙酰氧基)碘]苯 作用下， 生成 methyl (3-azido-4-methoxyphenyl)acetate
  参考文献：
  名称：

  用高价碘试剂，苯基碘（III）双（三氟乙酸盐）（PIFA）和三甲基硅烷基叠氮化物对芳族化合物进行新型氧化叠氮化

  摘要：

  一种新的有用的方法，可通过在1,1,1,3,3,3-六氟-2-丙醇中与高价碘试剂，苯基碘（III）双（三氟乙酸盐）（PIFA）反应，然后再进行芳香化反应开发了叠氮化三甲基甲硅烷基（TMSA）的处理方法。还讨论了可能的机制。

  DOI：

  10.1016/s0040-4039(00)92160-9

文献信息

• A novel oxidative azidation of aromatic compounds with hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl azide
  作者：Yasuyuki Kita、Hirofumi Tohma、Masanao Inagaki、Kenji Hatanaka、Takayuki Yakura

  DOI：10.1016/s0040-4039(00)92160-9

  日期：1991.1

  A novel and useful method for the azidation of aromatic compounds by the reaction of hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) in 1,1,1,3,3,3-hexafluoro-2-propanol followed by treatment of trimethylsilyl azide (TMSA) was developed. The possible mechanism is also discussed.

  一种新的有用的方法，可通过在1,1,1,3,3,3-六氟-2-丙醇中与高价碘试剂，苯基碘（III）双（三氟乙酸盐）（PIFA）反应，然后再进行芳香化反应开发了叠氮化三甲基甲硅烷基（TMSA）的处理方法。还讨论了可能的机制。
• Similarities and Differences in the Structure−Activity Relationships of Capsaicin and Resiniferatoxin Analogues
  作者：Christopher S. J. Walpole、Stuart Bevan、Graham Bloomfield、Robin Breckenridge、Iain F. James、Timothy Ritchie、Arpad Szallasi、Janet Winter、Roger Wrigglesworth

  DOI：10.1021/jm960139d

  日期：1996.1.1

  Structure-activity relationships in analogues of the irritant natural product capsaicin have previously been rationalized by subdivision of the molecule into three structural regions (A, B, and C). The hypothesis that resiniferatoxin (RTX), which is a high-potency ligand for the same receptor and which has superficial structural similarities with capsaicin, could be analogously subdivided has been investigated. The effects of making parallel changes in the two structural series have been studied in a cellular functional assay which is predictive of analgesic activity. Parallel structural changes in the two series lead to markedly different consequences on biological activity; the 3- and 4-position aryl substituents (corresponding to the capsaicin 'A-region') which are strictly required for activity in capsaicin analogues are not important in RTX analogues. The homovanillyl C-20 ester group in RTX (corresponding to the capsaicin 'B-region') is more potent than the corresponding amide, in contrast to the capsaicin analogues. Structural variations to the diterpene moiety suggest that the functionalized 5-membered diterpene ring of RTX is an important structural determinant for high potency. Modeling studies indicate that the 3D position of the alpha-hydroxy ketone moiety in the 5-membered ring is markedly different in the phorbol (inactive) analogues and RTX (active) series. This difference appears to be due to the influence of the strained ortho ester group in RTX, which acts as a local conformational constraint. The reduced activity of an analogue substituted in this region and the inactivity of a simplified analogue in which this unit is entirely removed support this conclusion.
• Hypervalent Iodine-Induced Nucleophilic Substitution of para-Substituted Phenol Ethers. Generation of Cation Radicals as Reactive Intermediates
  作者：Yasuyuki Kita、Hirofumi Tohma、Kenji Hatanaka、Takeshi Takada、Shigekazu Fujita、Shizue Mitoh、Hiromu Sakurai、Shigenori Oka

  DOI：10.1021/ja00088a003

  日期：1994.5

  A novel hypervalent iodine induced nucleophilic substitution of para-substituted phenol ethers in the presence of a variety of nucleophiles is described. UV and ESR spectroscopic studies indicate that this reaction proceeds via cation radicals, [ArH.+], as reactive intermediates generated by single-electron transfer (SET) from a charge-transfer (dT) complex of phenol ethers with phenyliodine(III) bis(trifluoroacetate) (PIFA). This is the first case that involves a radical intermediate on hypervalent iodine oxidations of aromatic compounds.