(4-(dimethylamino)phenyl) (3,4,5-trimethoxyphenyl)methanol | 189187-29-9

• 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: (4-(dimethylamino)phenyl) (3,4,5-trimethoxyphenyl)methanol
• 英文别名: [4-(Dimethylamino)phenyl]-(3,4,5-trimethoxyphenyl)methanol
• CAS: 189187-29-9
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: WNEKUKIRQCITRG-UHFFFAOYSA-N

物化性质

• 沸点：
  474.8±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-(dimethylamino)phenyl) (3,4,5-trimethoxyphenyl)methanol 在 重铬酸吡啶 、 三甲基氯硅烷 、 四丁基硫酸氢铵 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 (4-(dimethylamino)-3-(1,3-dioxolan-2-yl)phenyl) (3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Exploring the size adaptability of the B ring binding zone of the colchicine site of tubulin with para-nitrogen substituted isocombretastatins

  摘要：

  We have synthesized and assayed dimethylaminophenyl, pyrrolidin-1-ylphenyl and carbazole containing phenstatins and isocombretastatins as analogues of the highly potent indoleisocombretastatins with extended or reduced ring sizes. This is an attempt to explore beyond the structural constraints of the X-ray crystal structures the zone of the colchicine site where the tropolone ring of colchicine binds to tubulin (zone 1). The isocombretastatins display up to 30 fold increased water solubility when compared with combretastatin A-4, potent inhibition of tubulin polymerization, and nanomolar cytotoxicities against several human cancer cell lines irrespective of the size of the B ring. On the other hand, substitutions ortho to the nitrogen cause an important reduction in potency. We have also shown that representative compounds inhibit autophagy. These results show that zone 1 can adapt to systems of different size as far as they stay in a common plane, but does not tolerate substituents protruding above or below it. These results can help in the understanding of the binding modes of structures with similar systems and in the design of new colchicine site ligands. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.047
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 4-(N,N-二甲基)苯胺溴化镁 以 四氢呋喃 为溶剂， 反应 10.0h， 以73%的产率得到(4-(dimethylamino)phenyl) (3,4,5-trimethoxyphenyl)methanol
  参考文献：
  名称：

  First General Synthesis of (p-Nitroaryl)diarylmethanes via Vicarious Nucleophilic Substitution of Hydrogen

  摘要：

  A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quantitative condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence of perfluorocarbon fluids, followed by vicarious nucleophilic substitution of the resulting diarylmethylbenzotriazoles upon nitrobenzenes in moderate to high yield. Oxidative nucleophilic substitution of hydrogen is observed as a side process. These vicarious nucleophilic substitutions complement Friedel-Crafts reactions for the synthesis of triarylmethanes.

  DOI：

  10.1021/jo9624197

文献信息

• Disproportionation reaction of diarylmethylisopropyl ethers: a versatile access to diarylmethanes from diarylcarbinols speeded up by the use of microwave irradiation
  作者：Nathalie L'Hermite、Anne Giraud、Olivier Provot、Jean-François Peyrat、Mouâd Alami、Jean-Daniel Brion

  DOI：10.1016/j.tet.2006.09.083

  日期：2006.12

  An efficient synthesis of diarylmethanes under classical thermal conditions and under microwave heating is described from diarylcarbinols via a new disproportionation reaction. The key step involves a selective hydride transfer of isopropyl ether intermediates. Mild reaction conditions i.e., catalytic CBr4 or TfOH in i-PrOH and good yields render this method useful and competitive to the conventional

  描述了在二元芳基甲醇中通过新的歧化反应在经典的热条件下和在微波加热下的二芳基甲烷的有效合成。关键步骤涉及异丙醚中间体的氢化物选择性转移。温和的反应条件，即i -PrOH中的催化CBr 4或TfOH和良好的收率，使得该方法相对于依赖于外部还原剂应用的常规方法而言是有用的且具有竞争力。
• First General Synthesis of (<i>p</i>-Nitroaryl)diarylmethanes <i>via</i> Vicarious Nucleophilic Substitution of Hydrogen
  作者：Alan R. Katritzky、Dorin Toader

  DOI：10.1021/jo9624197

  日期：1997.6.13

  A general regiospecific method for the synthesis of (p-nitroaryl)diarylmethanes has been developed starting from diarylmethanols and 2- and/or 3-substituted nitrobenzenes. This utilizes the quantitative condensation between benzotriazole and diarylmethanols under acidic catalysis and in the presence of perfluorocarbon fluids, followed by vicarious nucleophilic substitution of the resulting diarylmethylbenzotriazoles upon nitrobenzenes in moderate to high yield. Oxidative nucleophilic substitution of hydrogen is observed as a side process. These vicarious nucleophilic substitutions complement Friedel-Crafts reactions for the synthesis of triarylmethanes.
• Exploring the size adaptability of the B ring binding zone of the colchicine site of tubulin with para-nitrogen substituted isocombretastatins
  作者：Carmen Jiménez、Younes Ellahioui、Raquel Álvarez、Laura Aramburu、Alejandra Riesco、Myriam González、Alba Vicente、Abdelaziz Dahdouh、Ahmed Ibn Mansour、Carlos Jiménez、Diego Martín、Rogelio G. Sarmiento、Manuel Medarde、Esther Caballero、Rafael Peláez

  DOI：10.1016/j.ejmech.2015.05.047

  日期：2015.7

  We have synthesized and assayed dimethylaminophenyl, pyrrolidin-1-ylphenyl and carbazole containing phenstatins and isocombretastatins as analogues of the highly potent indoleisocombretastatins with extended or reduced ring sizes. This is an attempt to explore beyond the structural constraints of the X-ray crystal structures the zone of the colchicine site where the tropolone ring of colchicine binds to tubulin (zone 1). The isocombretastatins display up to 30 fold increased water solubility when compared with combretastatin A-4, potent inhibition of tubulin polymerization, and nanomolar cytotoxicities against several human cancer cell lines irrespective of the size of the B ring. On the other hand, substitutions ortho to the nitrogen cause an important reduction in potency. We have also shown that representative compounds inhibit autophagy. These results show that zone 1 can adapt to systems of different size as far as they stay in a common plane, but does not tolerate substituents protruding above or below it. These results can help in the understanding of the binding modes of structures with similar systems and in the design of new colchicine site ligands. (C) 2015 Elsevier Masson SAS. All rights reserved.