Benzyl-<2-benzyl-4-methyl-phenyl>-aether | 100268-44-8

• 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: Benzyl-<2-benzyl-4-methyl-phenyl>-aether
• 英文别名: 2-benzyl-4-methylphenyl benzyl ether；benzyl-(2-benzyl-4-methyl-phenyl)-ether；Benzyl-(2-benzyl-4-methyl-phenyl)-aether；2-Benzyl-4-methyl-1-phenylmethoxybenzene
• CAS: 100268-44-8
• 化学式: C₂₁H₂₀O
• 分子量: 288.389
• InChiKey: CVDJLAUJLGJAPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  sodium 4-methylphenoxide 、 溴甲苯 在 苯 作用下， 生成 Benzyl-<2-benzyl-4-methyl-phenyl>-aether
  参考文献：
  名称：

  Alkylation of Cresol Salts. Use of Azo Coupling to Establish Orientation^1-3

  摘要：

  DOI：

  10.1021/jo01095a003

文献信息

• Heterogeneous Phase Alkylation of Phenols Making Use of Phase Transfer Catalysis and Microwave Irradiation
  作者：Gyorgy Keglevich、Erika Balint、Eva Karsai、Judit Varga、Alajos Grun、Maria Balint、Istvan Greiner

  DOI：10.2174/157017809789869500

  日期：2009.10.1

  The benzylation of cresol was studied under liquid-liquid and solid-liquid phase transfer catalytic conditions. Microwave irradiation was useful only in the solid-liquid phase benzylations. Using acetonitrile as the solvent, the benzylations were fully O-selective, but complete conversions were obtained only in the presence of Cs2CO3. There was no need to use an onium salt. In the absence of solvent, an O-selectivity of ca. 90% could be obtained in the presence of an alkali carbonate and an onium salt. The optimum set of conditions was extended to the reaction of other phenol derivatives and alkylating agents.

  苄基化反应在液液和固液相转移催化条件下对甲酚进行了研究。微波辐射仅在固液相苄基化反应中有用。使用乙腈作为溶剂，苄基化反应完全表现出O选择性，但在存在Cs2CO3的条件下才能获得完全转化。无需使用鎓盐。在没有溶剂的情况下，在碱金属碳酸盐和鎓盐的存在下，可以获得约90%的O选择性。最佳条件集合被扩展到其他酚类衍生物和烷基化剂的反应中。
• Chemoselectivity in the microwave-assisted solvent-free solid–liquid phase benzylation of phenols: O- versus C-alkylation
  作者：György Keglevich、Erika Bálint、Éva Karsai、Alajos Grün、Mária Bálint、István Greiner

  DOI：10.1016/j.tetlet.2008.06.051

  日期：2008.8

  The outcome of the solvent-free benzylation of phenol and 4-substituted phenols (such as 4-cresol and 4-chlorophenol) under MW irradiation was found to depend on the absence or presence of the base (K2CO3) and catalyst (triethylbenzylammonium chloride (TEBAC)). Reaction of benzyl halides at 80–120 °C in the presence of K2CO3 and TEBAC resulted in O-alkylation in high (89–96%) chemoselectivities. In

  发现在微波辐照下苯酚和4-取代的苯酚（例如4-甲酚和4-氯苯酚）的无溶剂苄化反应的结果取决于是否存在碱（K 2 CO 3）和催化剂（三乙基苄基氯化铵（TEBAC））。在存在K 2 CO 3和TEBAC的情况下，卤化苄在80–120°C的反应导致O-烷基化反应具有较高的化学选择性（89-96％）。在没有TEBAC的情况下，C-烷基化的比例相当大（16-34％）。也从反应混合物中省略了K 2 CO 3，C-烷基化变得占优势。在4-叔的情况下-丁基苯酚，TEBAC的存在促进了C-烷基化。烷基化的选择性可以通过选择适当的条件来微调。
• [EN] PROCESS FOR THE PRODUCTION OF 2-[4-(3- OR 2-FLUOROBENZYLOXY)BENZYLAMINO]PROPANAMIDES WITH HIGH PURITY DEGREE<br/>[FR] PROCÉDÉ DE PRODUCTION DE 2-[4-(3- OU 2-FLUOROBENZYLOXY)BENZYLAMINO] PROPANAMIDES D'UN DEGRÉ DE PURETÉ ÉLEVÉ
  申请人：NEWRON PHARM SPA

  公开号：WO2009074478A1

  公开（公告）日：2009-06-18

  A process for obtaining therapeutically active 2-[4-(3- and 2-(flurobenzyloxy)benzylamino]propanamides, and their salts with pharmaceutically acceptable acids with high purity degree, in particular, with a content of dibenzyl derivatives impurities lower than 0.03%, preferably lower than 0.01% by weight. The process is carried out by submitting the Schiff bases intermediates 2- [4 -(3- and 2-fluorobenzyloxy)benzylideneamino]propanamides to a reduction reaction with a reducing agent selected from sodium borohydride and potassium borohydride in an appropriate amount of an organic solvent selected from C1-C5 lower alkanols, allowing the formation and presence during a substantial position of the reduction reaction course of a suspension of the Schiff base into the saturated solution of the Schiff base into the same organic solvent.

  一种用于获得具有高纯度度的治疗活性2-[4-(3-和2-(氟苄氧基)苄基氨基]丙酰胺及其与药学上可接受的酸盐，特别是含二苄衍生物杂质低于0.03%，最好低于0.01%重量的方法。该过程通过将席夫碱中间体2-[4-(3-和2-氟苄氧基)苄亚胺]丙酰胺提交给还原剂（选择自硼氢化钠和硼氢化钾）的还原反应，在选择自C1-C5低级烷醇的有机溶剂中以适量进行，允许在还原反应过程中的实质位置形成和存在席夫碱的悬浮物，使其转变为席夫碱在相同有机溶剂中的饱和溶液。
• High purity degree 2-[4-(3- and 2-fluorobenzyloxy)benzylamino]propanamides for use as medicaments and pharmaceutical formulations containing them
  申请人：Newron Pharmaceuticals S.p.A.

  公开号：EP2474521A1

  公开（公告）日：2012-07-11

  High purity degree (S)-2-[4-(3- and 2-fluorobenzyloxy)-benzylamino]propanamides with a content of genotoxic dibenzyl derivatives impurities lower than 0.03%, preferably lower than 0.01%, by weight for use as safe medicaments and pharmaceutical composition containing them as the active agents.

  高纯度(S)-2-[4-(3-和 2-氟苄氧基)-苄基氨基]丙酰胺，其基因毒性二苄基衍生物杂质含量按重量计低于 0.03%，最好低于 0.01%，可用作安全的药物和含有它们作为活性剂的药物组合物。
• 579. The rearrangement of benzyl p-tolyl ether
  作者：N. M. Cullinane、R. A. Woolhouse、G. B. Carter

  DOI：10.1039/jr9620002995

  日期：——