2-((dibenzylamino)(phenyl)methyl)phenol

• 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-((dibenzylamino)(phenyl)methyl)phenol
• 英文别名: 2-[(Dibenzylamino)-phenylmethyl]phenol；2-[(dibenzylamino)-phenylmethyl]phenol
• 化学式: C₂₇H₂₅NO
• 分子量: 379.502
• InChiKey: LBWNXZYPUHOJFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  水杨醛 、 二苄胺 、 苯硼酸 反应 2.0h， 以85%的产率得到2-((dibenzylamino)(phenyl)methyl)phenol
  参考文献：
  名称：

  Microwave-Assisted Neat Procedure for the Petasis Reaction

  摘要：

  一种新的无溶剂微波辅助Petasis多组分反应方法被开发出来。这种方法首次将硼-曼尼希反应应用于无溶剂条件，并证明其适用于各种硼酸和仲胺。与传统方法相比，该方法反应时间短，收率很高。由于该方法效率高，从化学计量量的反应物开始，起始原料就能完全转化为预期产物，避免了通常在硅胶上进行耗溶剂的柱色谱法。除了水冲洗外，不需要其他纯化步骤。

  DOI：

  10.1055/s-0029-1218727

文献信息

• Magnetically Retrievable Nanocomposite Based on Thiosemicarbazide–Formaldehyde Resin as a Versatile Nucleophilic Scavenger
  作者：Maomin Zhen、Danfeng Zhang、Zeyu Zhang、Yanqing Peng

  DOI：10.1021/acscombsci.6b00090

  日期：2016.12.12

  retrievable nanocomposite was prepared by in situ polycondensation and entrapment of iron oxide nanoparticles. This material was found to be efficient in trapping excess electrophilic reagents such as carbonyl compounds, acid chlorides and isothiocyanates. Advantages of the new scavenger include facile preparation, high loading capacity, low cost, satisfactory swelling properties in polar solvents, and

  通过原位缩聚和包埋氧化铁纳米颗粒制备了可磁性回收的纳米复合材料。发现该材料可有效捕集过量的亲电试剂，例如羰基化合物，酰氯和异硫氰酸酯。新型清除剂的优点包括制备简便，装载量高，成本低，在极性溶剂中具有令人满意的溶胀性能以及方便的磁回收。
• Multicomponent Petasis-borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies
  作者：Íris Neto、Joana Andrade、A. S. Fernandes、Catarina Pinto Reis、Jagadish K. Salunke、Arri Priimagi、Nuno R. Candeias、Patrícia Rijo

  DOI：10.1002/cmdc.201600244

  日期：2016.9.20

  starting from salicylaldehyde and its derivatives. The obtained compounds were tested against a large panel of microorganisms, Gram-positive and Gram-negative bacteria, and a yeast. Among the several tertiary amine derivatives tested, indoline-derived aminophenols containing a nitro group at the para-phenol position showed considerable activity against bacteria tested with minimal inhibitory concentrations

  在这项工作中，我们报告了烷基氨基酚的抗菌活性。通过多组分Petasis-borono Mannich反应，从水杨醛及其衍生物开始，制备了一系列此类化合物。针对一大批微生物，革兰氏阳性和革兰氏阴性细菌以及酵母对获得的化合物进行了测试。在所测试的几种叔胺衍生物中，对苯酚位置含硝基的吲哚啉衍生氨基酚显示出对细菌的可观活性，对金黄色葡萄球菌和耻垢分枝杆菌的最低抑菌浓度低至1.36μm。仅在比抗菌活性所需的浓度高得多的浓度下才观察到新的对硝基苯酚衍生物的细胞毒性。
• 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。
• Microwave-Assisted Neat Procedure for the Petasis Reaction
  作者：Frédéric Lamaty、Pierrick Nun、Jean Martinez

  DOI：10.1055/s-0029-1218727

  日期：2010.6

  A new solvent-free microwave-assisted procedure for the Petasis multicomponent reaction was developed. This method is the first application of the borono-Mannich reaction in solvent-free conditions and proved its applicability to various boronic acids and secondary amines. Results are very good in term of yields with shorter reaction time than the classical methods. Because of the efficiency­ of the method, full conversion of the starting materials towards­ the expected product was achieved, starting from stoichiometric quantities of reactants, avoiding the usual solvent-consuming column chromatography on silica gel. No purification step other than an aqueous washing was required.

  一种新的无溶剂微波辅助Petasis多组分反应方法被开发出来。这种方法首次将硼-曼尼希反应应用于无溶剂条件，并证明其适用于各种硼酸和仲胺。与传统方法相比，该方法反应时间短，收率很高。由于该方法效率高，从化学计量量的反应物开始，起始原料就能完全转化为预期产物，避免了通常在硅胶上进行耗溶剂的柱色谱法。除了水冲洗外，不需要其他纯化步骤。
• Microwave assisted Petasis boronic-Mannich reactions
  作者：Neville J. McLean、Heather Tye、Mark Whittaker

  DOI：10.1016/j.tetlet.2003.11.092

  日期：2004.1

  We have used a design of experiments (DOE) approach to optimise rapidly a set of microwave assisted conditions for the Petasis reaction. The optimal conditions involved the microwave heating of the reaction components in dichloromethane (1 M concentration) at 120 degreesC for 10 min in a focussed microwave (CEM Explorer). These conditions were successfully applied to a range of Petasis reactions employing either glyoxylic acid or salicylaldehyde as the carbonyl component along with a number of aryl/heteroaryl boronic acids and amine components. (C) 2003 Elsevier Ltd. All rights reserved.