1-{4-[3-(4-chlorophenoxy)-2-hydroxypropoxy]phenyl}-1-ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{4-[3-(4-chlorophenoxy)-2-hydroxypropoxy]phenyl}-1-ethanone
• 英文别名: 1-{4-[3-(4-chlorophenoxy)-2-hydroxypropoxy]phenyl}ethanone；1-[4-[3-(4-Chlorophenoxy)-2-hydroxypropoxy]phenyl]ethanone
• 化学式: C₁₇H₁₇ClO₄
• 分子量: 320.773
• InChiKey: JWXMVIOOFLGOKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 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：

  4-氯苯基缩水甘油醚 、 对羟基苯乙酮 在 四丁基溴化铵 、 potassium carbonate 、 palladium dichloride 作用下， 以 水 为溶剂， 反应 2.0h， 以86%的产率得到1-{4-[3-(4-chlorophenoxy)-2-hydroxypropoxy]phenyl}-1-ethanone
  参考文献：
  名称：

  钯纳米粒子协同双活化催化酚类化合物的环氧化物开环。

  摘要：

  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。

  DOI：

  10.1039/c3cc42507j

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。
• Highly Regioselective Ring Opening of Oxiranes with Phenoxides in the Presence of β-Cyclodextrin in Water
  作者：K. Surendra、N. Srilakshmi Krishnaveni、Y. V. D. Nageswar、K. Rama Rao

  DOI：10.1021/jo034194n

  日期：2003.6.1

  Highly regioselective ring opening of oxiranes to beta-hydroxy ethers with phenoxides has been achieved in impressive yields in the presence of beta-cyclodextrin as catalyst and water as solvent.

  在以β-环糊精为催化剂和以水为溶剂的情况下，已以令人印象深刻的收率实现了氧杂环戊烷对苯酚类化合物对β-羟基醚的高区域选择性开环。
• An efficient catalyst-free regio- and stereoselective ring-opening of epoxides with phenoxides using polyethylene glycol as the reaction medium
  作者：Biswanath Das、Maddeboina Krishnaiah、Ponnaboina Thirupathi、Keetha Laxminarayana

  DOI：10.1016/j.tetlet.2007.04.062

  日期：2007.6

  A catalyst-free regio- and stereoselective ring-opening of epoxides with phenoxides has been carried out efficiently using polyethylene glycol as the reaction medium to form the corresponding β-aryloxyalcohols in high yields at room temperature.

  使用聚乙二醇作为反应介质，可以在室温下高收率地高效地进行环氧化物与酚盐的无催化剂的区域和立体选择性开环反应。
• 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.