2-(morpholino(p-tolyl)methyl)phenol | 1031940-06-3

• 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: 2-(morpholino(p-tolyl)methyl)phenol
• 英文别名: 2-[(4-Methylphenyl)-morpholin-4-ylmethyl]phenol
• CAS: 1031940-06-3
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: XASGNSFJUKUUJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 在 盐酸 作用下， 以 水 为溶剂， 反应 14.6h， 生成 2-(morpholino(p-tolyl)methyl)phenol
  参考文献：
  名称：

  Sequential One-Pot Access to Molecular Diversity through Aniline Aqueous Borylation

  摘要：

  On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

  DOI：

  10.1021/jo501665e

文献信息

• Chitosan: highly efficient, green, and reusable biopolymer catalyst for the synthesis of alkylaminophenols via Petasis borono–Mannich reaction
  作者：Sirigi Reddy Sudharsan Reddy、Bhoomireddy Rajendra Prasad Reddy、Peddiahgari Vasu Govardhana Reddy

  DOI：10.1016/j.tetlet.2015.07.004

  日期：2015.8

  nafion® 117, PEG-OSO3H, tween® 80, poly styrene –SO3H and chitosan for the preparation of alkylaminophenols through Petasis borono–Mannich reaction by one-pot three component condensation of o-hydroxy aldehydes, secondary amines, and various boronic acids. It was observed that the reaction was completed in a short period of time and the yield was optimum by virtue of chitosan heterogeneous catalyst. Furthermore

  我们筛选了不同的功能化聚合催化剂，如nafion®117，PEG-OSO 3 H，tween®80，聚苯乙烯–SO 3 H和壳聚糖，通过一锅三锅法通过波塔西斯·波罗诺–曼尼希反应制备烷基氨基酚的催化功效。邻羟基醛，仲胺和各种硼酸的组分缩合。观察到反应在短时间内完成，并且由于壳聚糖非均相催化剂的产率是最佳的。此外，可以通过简单的过滤来回收催化剂，并且可以重复使用多达十个循环。从重复使用的第六个周期开始观察到催化活性的平稳损失。
• Three-component, solvent-free synthesis of Betti base catalyzed by sulfated polyborate
  作者：Manisha S. Patil、Chetan K. Khatri、Ganesh U. Chaturbhuj

  DOI：10.1007/s00706-018-2169-z

  日期：2018.8

  this work, efficient, mild, and eco-friendly procedure of 1-aminoalkyl-2-phenol/Betti base from one-pot three-component condensations of aldehyde, phenol, and morpholine in the presence of sulfated polyborate catalyst, under a solvent-free condition at 100 °C, is described. The key advantages of the present method are short reaction time, high yields, aqueous work-up procedure, low cost, stable, reusable

  摘要在这项工作中，在溶剂化硫酸多硼酸盐催化剂存在下，由一锅三元乙醛，苯酚和吗啉的缩合反应制得的1-氨基烷基-2-苯酚/贝蒂碱的高效，温和和环保的方法描述了100°C时的无条件状态。本方法的主要优点是反应时间短，产率高，水后处理程序，成本低，稳定，可重复使用的催化剂和无溶剂的反应条件。 图形概要
• Solvent‐free Synthesis of Alkylaminophenols via Petasis Boronic Mannich Reaction in One Pot without Catalysts
  作者：Ying Liu、Limin Wang、Yuanyuan Sui、Jianjun Yu

  DOI：10.1002/cjoc.201090340

  日期：2010.10

  By using solvent‐free and heat conditions, the Petasis boronic Mannich reaction of salicylaldehydes with various boronic acids and secondary amines without catalyst is described. The alkylaminophenols were obtained in moderate to good yields in a shorter reaction time than the traditional methods.

  通过使用无溶剂和加热条件，描述了水杨醛与各种硼酸和仲胺在没有催化剂的情况下的Petasis硼酸曼尼希反应。与传统方法相比，在较短的反应时间内以中等至良好的收率获得了烷基氨基酚。
• Glycerol as an Efficient Medium for the Petasis Borono-Mannich Reaction
  作者：Tomi Rosholm、Pedro M. P. Gois、Robert Franzen、Nuno R. Candeias

  DOI：10.1002/open.201402066

  日期：2015.2

  provided the reaction product in higher yield. Crude glycerol, as generated by the biodiesel industry, was evaluated and found to be a suitable solvent for the PBM reaction, successfully expanding the potential use of this industry by‐product. Based on density functional theory (DFT) calculations and the obtained experimental results, the involvement of glycerol‐derived boronic esters in the reaction mechanism

  多组分Petasis borono–Mannich（PBM）反应是从硼酸，醛/酮和胺一步制备复杂分子的有用工具。在这里，我们描述了甘油在水杨醛或2-吡啶甲醛与几种硼酸和仲胺的PBM反应中的使用。从这些容易获得的起始原料中，烷基氨基酚，2-取代的吡啶和2 H色烯的制备以合理至高收率的方式进行。将甘油与其他溶剂进行了比较，在某些情况下，甘油以更高的产率提供了反应产物。对生物柴油行业产生的粗制甘油进行了评估，发现它是用于PBM反应的合适溶剂，成功扩大了该行业副产品的潜在用途。根据密度泛函理论（DFT）计算和获得的实验结果，表明甘油衍生的硼酸酯在反应机理中的参与与游离硼酸途径竞争。对于这两种机理，都确定了芳基从硼酸根迁移至亚胺基的相似吉布斯自由能。
• Water: A Suitable Medium for the Petasis Borono-Mannich Reaction
  作者：Nuno R. Candeias、Luís F. Veiros、Carlos A. M. Afonso、Pedro M. P. Gois

  DOI：10.1002/ejoc.200900056

  日期：——

  Water was used as the solvent in the Petasis borono-Mannich reaction. With the use of salicylaldehyde, secondary amines and boronic acids, several alkylaminophenols were obtained in considerably high yields in water. By using the same methodology, 2H-chromenes were prepared with the use of vinyl boronic acids. The reaction mechanism was studied by DFT calculations, and the results obtained corroborate

  Petasis 硼-曼尼希反应中使用水作为溶剂。使用水杨醛、仲胺和硼酸，在水中以相当高的收率获得了几种烷基氨基苯酚。通过使用相同的方法，使用乙烯基硼酸制备 2H-色烯。通过DFT计算研究了反应机理，所得结果证实了实验观察到的溶剂效应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)