4-[3-(4-chlorophenoxy)-2-hydroxypropoxy]benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[3-(4-chlorophenoxy)-2-hydroxypropoxy]benzaldehyde
• 英文别名: 4-[3-(4-Chlorophenoxy)-2-hydroxypropoxy]benzaldehyde
• 化学式: C₁₆H₁₅ClO₄
• 分子量: 306.746
• InChiKey: UJCOQJWMVSJFBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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 、 对羟基苯甲醛 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4-[3-(4-chlorophenoxy)-2-hydroxypropoxy]benzaldehyde
  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

• Bi(OTf)₃-catalyzed Regioselective Ring Opening of Epoxides with Phenols: Facile Synthesis of 1,3-Diaryloxy-2-propanols
  作者：Ahmed Kamal、Syed Kaleem Ahmed、Mahendra Sandbhor、Mohammed Naseer Ahmed Khan、Mohammed Arifuddin

  DOI：10.1246/cl.2005.1142

  日期：2005.8

  Substituted aryl oxiranes undergo the facile ring opening with phenols in the presence of catalytic amount of bismuth(III) triflate to afford 1,3-diaryloxy-2-propanols in excellent yields under mild conditions. Bismuth(lll) triflate is relatively nontoxic, easy to handle and inexpensive, which makes this procedure particularly attractive for large scale synthesis.

  在催化量的三氟甲磺酸铋 (III) 存在下，取代的芳基环氧乙烷与酚类轻松开环，在温和条件下以优异的产率得到 1,3-二芳氧基-2-丙醇。三氟甲磺酸铋 (III) 相对无毒、易于处理且价格低廉，这使得该程序对大规模合成特别有吸引力。
• 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.