1-(2'-methylphenoxy)-3-(phenylamino)propan-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2'-methylphenoxy)-3-(phenylamino)propan-2-ol
• 英文别名: 1-(o-tolyloxy)-3-(phenylamino)propan-2-ol；1-(phenylamino)-3-(o-tolyloxy)propan-2-ol；1-phenylamino-3-o-tolyloxy-propan-2-ol；1-anilino-3-(2-methylphenoxy)propan-2-ol
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: JOPFIGNAPKJSRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲苯缩水甘油醚 、 苯胺 在 iron oxide 作用下， 以 neat (no solvent) 为溶剂， 反应 20.0h， 以70%的产率得到1-(2'-methylphenoxy)-3-(phenylamino)propan-2-ol
  参考文献：
  名称：

  磁性纳米 Fe3O4 催化胺对环氧化物的无溶剂立体和区域选择性氨解；一种合成β-氨基醇的绿色方法

  摘要：

  我们报告了使用磁性纳米 Fe3O4 作为温和的多相催化剂，用于环氧化物与胺的氨解。该方法构成了一种在无溶剂和环境反应条件下形成具有非常高立体选择性和区域选择性的各种 β-氨基醇的绿色方法。手性环氧化物与胺的氨解得到相应的手性 β-氨基醇，立体化学完全反转。磁性纳米Fe3O4催化剂易于回收和循环利用。

  DOI：

  10.1055/s-0033-1340844

文献信息

• Microwave-Enhanced Sulphated Zirconia and SZ/MCM-41 Catalyzed Regioselective Synthesis of β-Amino Alcohols Under Solvent-Free Conditions
  作者：Guillermo Negrón-Silva、C. Hernández-Reyes、Deyanira Angeles-Beltrán、Leticia Lomas-Romero、Eduardo González-Zamora

  DOI：10.3390/molecules13040977

  日期：——

  A solvent-free approach for the regioselective synthesis of β-amino alcohols inshorter reaction times and higher yields, compared to conventional heating is described. Itinvolves microwave (MW) exposure of undiluted reactants in the presence of sulphatedzirconia (SZ) or sulphated zirconia over MCM-41 (SZM) as catalyst. Both acid materialscan be easily recovered and reused.

  本文介绍了一种无溶剂方法，与传统加热法相比，它能以更短的反应时间和更高的产率进行 β-氨基醇的区域选择性合成。该方法涉及在硫酸化锆 (SZ) 或硫酸化锆包覆 MCM-41 (SZM) 作为催化剂的情况下，对未稀释的反应物进行微波 (MW) 暴露。这两种酸性材料都很容易回收和重复使用。
• Comparative Study of Regioselective Synthesis of β-Aminoalcohols under Solventless Conditions Catalyzed by Sulfated Zirconia and SZ/MCM-41
  作者：Guillermo Negrón-Silva、C. Hernández-Reyes、Deyanira Angeles-Beltrán、Leticia Lomas-Romero、Eduardo González-Zamora、Juan Méndez-Vivar

  DOI：10.3390/12112515

  日期：——

  Sulfated zirconia and SZ/MCM-41 were used as catalysts for the synthesis of β-aminoalcohols via epoxide aminolysis. Sulfated zirconia was prepared by sol-gel andSZ/MCM-41 was obtained by impregnation. Solid catalysts were characterized by XRD,SEM-EDS, UV-Vis, FT-IR pyridine desorption and Nitrogen physisorption. Both acidmaterials were useful as catalysts, even when they were recycled several times. The β-aminoalcohols were characterized by FT-IR, 1H- and 13C-NMR and GC-MS.

  硫酸化氧化锆和 SZ/MCM-41 被用作催化剂，通过环氧化物氨解合成 β-氨基醇。硫酸化氧化锆通过溶胶-凝胶法制备，SZ/MCM-41 通过浸渍法制备。固体催化剂通过 XRD、SEM-EDS、UV-Vis、FT-IR 吡啶解吸和氮物理吸附进行了表征。这两种酸性材料作为催化剂都很有用，甚至可以多次循环使用。傅立叶变换红外光谱、1H- 和 13C-NMR 以及气相色谱-质谱对 β-氨基丙醇进行了表征。
• An Efficient Method for the Ring Opening of Epoxides with Aromatic Amines by Sb(III) Chloride under Microwave Irradiation
  作者：Dadkhoda Ghazanfari、Mohammed M. Hashemi、Mohammad Mehdi Mottaghi、Mohammad Mehdi Foroughi

  DOI：10.3184/030823408x313582

  日期：2008.4

  SbCl₃ supported on montmorillonite K-10 is an efficient catalyst for the ring opening of epoxides with aromatic amines under solvent-free conditions and microwave irradiation to give the corresponding β-amino alcohols in high yields with high regioselectivity

  在无溶剂和微波辐照条件下，蒙脱石 K-10 上支撑的 SbCl3 是环氧化物与芳香胺开环的高效催化剂，可高产率、高区域选择性地得到相应的 β-氨基醇
• Thiourea catalyzed aminolysis of epoxides under solvent free conditions. Electronic control of regioselective ring opening
  作者：Swapandeep Singh Chimni、Neeraj Bala、Vaibhav A. Dixit、Prasad V. Bharatam

  DOI：10.1016/j.tet.2010.02.053

  日期：2010.4

  A reactant economizing process for the regioselective aminolysis of epoxides using equimolar quantities of reactants catalyzed by the double hydrogen bond donor N,N'-bis[3,5-bis(trifluoromethyl)phenyl]thiourea is reported. Regioselectivity of the reaction is controlled by the electronic nature of the substituent on the styrene oxide, which has been substantiated on the basis of C-13 NMR data and DFT calculations. (C) 2010 Elsevier Ltd. All rights reserved.
• Solvent-free aminolysis of aliphatic and aryloxy epoxides with sulfated zirconia as solid acid catalyst
  作者：Arpan K. Shah、Manish Kumar、Sayed H.R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1016/j.apcata.2014.08.024

  日期：2014.9

  Single-step and two-steps synthetic procedure for the synthesis of sulfated zirconia (SZ) was developed, which were calcined at 500, 600 and 700 degrees C and characterized by various physico-chemical methods such as PXRD, FTIR, surface area, microanalysis, NH3-TPD and DRIFT analysis. These SZ materials were then employed as solid acid catalysts for the aminolysis of different aliphatic/aromatic terminal, aryloxy and meso epoxides with aromatic and aliphatic amines under ambient conditions. Amongst the catalyst prepared, SZ-2-600 prepared in two-steps and 600 degrees C calcined was found to be the most efficient catalyst to give beta-amino alcohols in up to 98% yield and >99% regioselectivity. The SZ catalyst was successfully recycled and reused up to six catalytic runs with intact efficiency. (C) 2014 Elsevier B.V. All rights reserved.