1-[2-(2'-hydroxy-3-phenoxypropoxy)phenyl]ethanone | 1260374-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-(2'-hydroxy-3-phenoxypropoxy)phenyl]ethanone
• 英文别名: 1-[2-(2-hydroxy-3-phenoxypropoxy)phenyl]ethanone；1-[2-(2-Hydroxy-3-phenoxypropoxy)phenyl]ethanone
• CAS: 1260374-20-6
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: NWDWANURBSLSFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基缩水甘油醚 、 2'-羟基苯乙酮 在 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene (PS-BEMP; PS = 200-400 mesh polystyryl with 2percent of divinylbenzene) 作用下， 反应 55.0h， 以97%的产率得到1-[2-(2'-hydroxy-3-phenoxypropoxy)phenyl]ethanone
  参考文献：
  名称：

  2-叔丁基氨基-2-二乙氨基-1,3-二甲基过氢-1,3,2-二氮杂磷负载在聚苯乙烯（PS-BEMP）上，作为无溶剂条件下环氧乙烷的苯酚脱苯反应的高效可回收和可重复使用的催化剂

  摘要：

  2叔聚苯乙烯（PS-BEMP）上负载的-Butylimino-2-二乙氨基-1,3-二甲基过氢-1,3,2-二氮杂膦是一种有效的催化剂，用于使环氧化物与酚（1.0当量）开环。已经获得了优异的产率，并且在大多数情况下，最终产物已经以纯净的形式分离出来，而无需任何额外的纯化步骤。与该协议相关的E因子很小，并且通过设置在无溶剂条件下运行的循环连续流反应器（SolFC）获得了进一步的改进，这使我们能够最大限度地减少浪费并将E因子与批处理条件相比减少了95％ 。另外，已经实现了2，3-二氢苯并[1，4]二氧杂环戊烯-5-酮的代表性合成。通过建立基于酚醛化方法的自动化多步连续流反应器并随后通过反应混合物的热处理进行内酯化来实现此过程的优化。3-Phenoxymethyl-2,3-dihydrobenzo [e [[1,4] dioxepin-5-one）以纯克形式和多克级分离，总收率非常令人满意，为86％，E因子为1

  DOI：

  10.1002/adsc.201000375

文献信息

• Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols
  作者：Kapileswar Seth、Sudipta Raha Roy、Bhavin V. Pipaliya、Asit K. Chakraborti

  DOI：10.1039/c3cc42507j

  日期：——

  Synergistic dual activation catalysis has been devised for epoxide phenolysis wherein palladium nanoparticles induce electrophilic activation via coordination with the epoxide oxygen followed by nucleophilic activation through anion-pi interaction with the aromatic ring of the phenol, and water (reaction medium) also renders assistance through 'epoxide-phenol' dual activation.

  已经设计了用于环氧酚醛化的协同双重活化催化，其中钯纳米颗粒通过与环氧氧的配位而诱导亲电活化，然后通过与苯酚的芳香环的阴离子-π相互作用进行亲核活化，并且水（反应介质）也通过“环氧-苯酚的双重活化。
• Silver nanoparticle-catalysed phenolysis of epoxides under neutral conditions: Scope and limitations of metal nanoparticles and applications towards drug synthesis
  作者：Kapileswar Seth、Sudipta Raha Roy、Damodara N. Kommi、Bhavin V. Pipaliya、Asit K. Chakraborti

  DOI：10.1016/j.molcata.2014.05.011

  日期：2014.10

  Chemo- and regio-selective epoxide phenolysis is reported for the first time under neutral condition catalysed by silver nanoparticles. Other metal nanoparticles (e.g., Au, Pd, Cu, In, and Ru) are less effective. The choice of solvent is critical with 2-propanol being the best followed by DEF. Amongst various stabilisers used (surfactants, PEGs, tetra-allcylammonium halides) the tetra-alkylammonium halides are found to be the most effective (TBAF > TBAB > TBACl > TBAI). The role of the silver nanoparticles is envisaged as synchronous mode epoxide-phenol dual activation via a cooperative network of coordination, anion-it interaction, and hydrogen bond. The silver nanoparticles are recovered and reused for five consecutive times. The reaction has been used for the synthesis of propranolol and naftopidil as a few representative cardiovascular drugs. (C) 2014 Published by Elsevier B.V.
• 2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2- diazaphosphorine Supported on Polystyrene (PS-BEMP) as an Efficient Recoverable and Reusable Catalyst for the Phenolysis of Epoxides under Solvent-Free Conditions
  作者：Artis Zvagulis、Simona Bonollo、Daniela Lanari、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1002/adsc.201000375

  日期：2010.10.4

  setting a cyclic continuous-flow reactor operating under solvent-free conditions (SolFC) that allowed us to minimize waste and reduce the E-factor by 95% compared to batch conditions. In addition the representative synthesis of a 2,3-dihydrobenzo[1,4]dioxepin-5-one has been realized. Optimization of this process was achieved by setting up an automated multi-step continuous-flow reactor based on a phenolysis

  2叔聚苯乙烯（PS-BEMP）上负载的-Butylimino-2-二乙氨基-1,3-二甲基过氢-1,3,2-二氮杂膦是一种有效的催化剂，用于使环氧化物与酚（1.0当量）开环。已经获得了优异的产率，并且在大多数情况下，最终产物已经以纯净的形式分离出来，而无需任何额外的纯化步骤。与该协议相关的E因子很小，并且通过设置在无溶剂条件下运行的循环连续流反应器（SolFC）获得了进一步的改进，这使我们能够最大限度地减少浪费并将E因子与批处理条件相比减少了95％ 。另外，已经实现了2，3-二氢苯并[1，4]二氧杂环戊烯-5-酮的代表性合成。通过建立基于酚醛化方法的自动化多步连续流反应器并随后通过反应混合物的热处理进行内酯化来实现此过程的优化。3-Phenoxymethyl-2,3-dihydrobenzo [e [[1,4] dioxepin-5-one）以纯克形式和多克级分离，总收率非常令人满意，为86％，E因子为1