3-(N-methyl-4-nitro-anilino)-propane-1,2-diol | 857390-67-1

• 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: 3-(N-methyl-4-nitro-anilino)-propane-1,2-diol
• 英文别名: 3-(N-Methyl-4-nitro-anilino)-propan-1,2-diol；3-(N-methyl-4-nitroanilino)propane-1,2-diol
• CAS: 857390-67-1
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: GWGNXSFGJRTJGC-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  429.6±24.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-苯二硼酸 、 3-(N-methyl-4-nitro-anilino)-propane-1,2-diol 以 甲苯 为溶剂， 反应 1.0h， 以82%的产率得到N-methyl-N-[[2-[4-[4-[(N-methyl-4-nitroanilino)methyl]-1,3,2-dioxaborolan-2-yl]phenyl]-1,3,2-dioxaborolan-4-yl]methyl]-4-nitroaniline
  参考文献：
  名称：

  Chiral 1,2- and 1,3-Diol-Functionalized Chromophores as Lego Building Blocks for Coupled Structures

  摘要：

  Chiral nitroanilines containing 1,2- or 1,3-diol functionalities have been synthesized by nucleophilic aromatic substitution of fluoronitroanilines with 1-aminopropane-2,3-diols and 2-aminopropane-1,3-diol in the melt. X-ray structure analyses confirm retention of the configuration of the chiral center. The novel chromophores are suitable to link reversibly to various substituted arylboronic acids which allows the construction of new solvatochromic sensor molecules suitable to response to solvent and anion coordination by fluoride. The solvatochromism of the new compounds has been studied using the Kamlet-Taft LSE relationship.

  DOI：

  10.1021/jo051097g
• 作为产物：
  描述：

  1-methylamino-3-(4-nitro-phenoxy)-propan-2-ol 在 sodium hydroxide 作用下， 生成 3-(N-methyl-4-nitro-anilino)-propane-1,2-diol
  参考文献：
  名称：

  Petrow; Stephenson, Journal of Pharmacy and Pharmacology, 1953, vol. 5, p. 359,366

  摘要：

  DOI：

文献信息

• Influence of the Boron Atom on the Solvatochromic Properties of 4-Nitroaniline-Functionalized Boronate Esters
  作者：Katja Hofmann、Stefan Spange

  DOI：10.1021/jo300530k

  日期：2012.6.1

  para-substituted phenylboronic acids [R2–C6H4–B(OH)2; R2 = −OCH3, −CH3, −H, −Br, −CHO, −NO2, −B(OH)2], and the solvatochromic properties of these esters are investigated in 33 solvents of different polarity. To interpret the solvent effects, the established linear solvation energy (LSE) multiparameter equations of Kamlet–Taft and the improved Catalán scales are used. Although the boron atom is separated

  对位与外围1,2-和1,3-二醇官能团[硝基苯胺衍生物ø 2 N-C 6 H ^ 4 -NR 1 -CH 2 CH（OH）CH 2 OH; O 2 N-C 6 H 4 -NR 1 -CH（CH 2 OH）2；共价键合在氨基上的R 1 = -H，-CH 3 ]被各种对位取代的苯基硼酸[R 2 -C 6 H 4 -B（OH）2酯化。R 2 = -OCH 3，-CH分别在33种极性不同的溶剂中研究了3，-H，-Br，-CHO，-NO 2，-B（OH）2的溶剂溶变色性质。为了解释溶剂效应，使用了建立的Kamlet-Taft线性溶剂化能量（LSE）多参数方程式和改进的Catalán标度。尽管硼原子与实际发色团被两个或三个sp 3-杂化碳原子隔开，但溶剂作用是给体，溶剂化作用对硝基苯胺单元具有显着的正溶剂化变色作用（R 1 = -CH 3）在硼原子上。取代基R 2对系数b的影响根据Kamlet-Taf
• Chiral 1,2- and 1,3-Diol-Functionalized Chromophores as Lego Building Blocks for Coupled Structures
  作者：Stefan Spange、Katja Hofmann、Bernhard Walfort、Tobias Rüffer、Heinrich Lang

  DOI：10.1021/jo051097g

  日期：2005.10.1

  Chiral nitroanilines containing 1,2- or 1,3-diol functionalities have been synthesized by nucleophilic aromatic substitution of fluoronitroanilines with 1-aminopropane-2,3-diols and 2-aminopropane-1,3-diol in the melt. X-ray structure analyses confirm retention of the configuration of the chiral center. The novel chromophores are suitable to link reversibly to various substituted arylboronic acids which allows the construction of new solvatochromic sensor molecules suitable to response to solvent and anion coordination by fluoride. The solvatochromism of the new compounds has been studied using the Kamlet-Taft LSE relationship.
• Petrow; Stephenson, Journal of Pharmacy and Pharmacology, 1953, vol. 5, p. 359,366
  作者：Petrow、Stephenson

  DOI：——

  日期：——