1-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N,N,N-trimethylmethanaminium iodide | 1089186-95-7

• 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: 1-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N,N,N-trimethylmethanaminium iodide
• 英文别名: (3-Fluoro-4-hydroxy-5-methoxyphenyl)methyl-trimethylazanium;iodide
• CAS: 1089186-95-7
• 化学式: C₁₁H₁₇FNO₂*I
• 分子量: 341.164
• InChiKey: RJUIJKRKBMRNPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.25
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N,N,N-trimethylmethanaminium iodide 在 盐酸 、 乌洛托品 、 四丁基硫酸氢铵 、 溶剂黄146 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 3-氟-4,5-二甲氧基苯甲醛
  参考文献：
  名称：

  Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues

  摘要：

  A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 degrees C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

  DOI：

  10.1055/s-0034-1379481
• 作为产物：
  描述：

  2-氟-6-甲氧基苯酚 以 乙醇 、 氯仿 为溶剂， 反应 2.0h， 生成 1-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N,N,N-trimethylmethanaminium iodide
  参考文献：
  名称：

  Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues

  摘要：

  A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 degrees C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

  DOI：

  10.1055/s-0034-1379481

文献信息

• The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands
  作者：Kwang Su Lim、Hobin Lee、Sung Eun Kim、Tae-Hwan Ha、Jihyae Ann、Karam Son、Sun Choi、Wei Sun、Larry V. Pearce、Ian A. DeAndrea-Lazarus、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.ejmech.2013.07.042

  日期：2013.10

  A series of carbonate analogues of 5'-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX: (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with K-i(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism. (C) 2013 Elsevier Masson SAS. All rights reserved.
• CLARK M. T.; ADEJARE A.; SHAMS G.; FELLER D. R.; MILLER D. D., J. MED. CHEM., 30,(1987) N 1, 86-90
  作者：CLARK M. T.、 ADEJARE A.、 SHAMS G.、 FELLER D. R.、 MILLER D. D.

  DOI：——

  日期：——