(+/-)-1-iodo-3-(4-methoxyphenyloxy)-2-propanol | 140647-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-1-iodo-3-(4-methoxyphenyloxy)-2-propanol
• 英文别名: 1-iodo-3-(4-methoxy-phenoxy)-propan-2-ol；1-iodo-3-(4-methoxyphenoxy)-2-propanol；1-(p-tolyloxy)-3-iodo-2-propanol；1-Iodo-3-(4-methoxyphenoxy)propan-2-ol
• CAS: 140647-13-8
• 化学式: C₁₀H₁₃IO₃
• 分子量: 308.116
• InChiKey: KCOVSCCCNSNLNX-UHFFFAOYSA-N

物化性质

• 沸点：
  374.8±37.0 °C(Predicted)
• 密度：
  1.646±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1-iodo-3-(4-methoxyphenyloxy)-2-propanol 生成 (+/-)-1-iodo-3-(4-methoxyphenyloxy)-2-propanol
  参考文献：
  名称：

  Resolution of Racemic O-(4-Methoxyphenyl)glycidol

  摘要：

  Racemic O-(4-methoxyphenyl)glycidol has been resolved in three steps by employing lipase mediated kinetic acylation of the halohydrin intermediates.

  DOI：

  10.3987/com-91-5934
• 作为产物：
  描述：

  4-甲氧基苯酚 在 sodium hydroxide 、 四甲基氯化铵 、 溶剂黄146 、 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 7.25h， 生成 (+/-)-1-iodo-3-(4-methoxyphenyloxy)-2-propanol
  参考文献：
  名称：

  Resolution of Racemic O-(4-Methoxyphenyl)glycidol

  摘要：

  Racemic O-(4-methoxyphenyl)glycidol has been resolved in three steps by employing lipase mediated kinetic acylation of the halohydrin intermediates.

  DOI：

  10.3987/com-91-5934

文献信息

• The halogen-mediated opening of epoxides in the presence of pyridine-containing macrocycles
  作者：Hashem Sharghi、Khodabakhsh Niknam、Maryam Pooyan

  DOI：10.1016/s0040-4020(01)00443-4

  日期：2001.7

  The ring opening of epoxides with elemental iodine and bromine in the presence of three pyridine-containing macrocyclic diamides as new catalysts affords vicinal iodo alcohols and bromo alcohols in high yields. This new procedure occurs regioselectively under mild conditions in various aprotic solvents. The catalysts are easily recovered and can be reused several times.

  在作为新催化剂的三种含吡啶大环二酰胺的存在下，环氧化物与元素碘和溴的开环提供了高产率的邻位碘代醇和溴代醇。这种新方法在温和条件下在各种非质子传递溶剂中区域选择性地发生。催化剂易于回收，可以重复使用多次。
• Protective opening of epoxide using pivaloyl halides under catalyst-free conditions
  作者：Chitturi Bhujanga Rao、Dasireddi Chandra Rao、Mallem Venkateswara、Yenamandra Venkateswarlu

  DOI：10.1039/c1gc15506g

  日期：——

  An efficient and environmentally benign protocol for protective opening of epoxide (POE) with pivaloyl halides in solvent-free conditions and in aqueous media under catalyst-free conditions has been developed. The green reaction conditions, simple work-up procedures, high yields and broad scope of the reaction illustrate the good synthetic utility of this method. The key advantages of the reaction are regioselectivity and reconvertability of products into their prior epoxides in the presence of mild reaction conditions.

  在无溶剂条件下和无催化剂条件下的水介质中，开发出了一种高效且对环境无害的环氧化物（POE）与特戊酰卤保护性开环方法。绿色的反应条件、简单的操作步骤、高产率和广泛的反应范围说明了这种方法的良好合成用途。该反应的主要优点是具有区域选择性，而且在温和的反应条件下，产物可重新转化为其先前的环氧化物。
• Green Protocol for the Synthesis of<i>vicinal</i>-Halohydrins from Oxiranes Using the [Bmim]PF₆/LiX Reagent System
  作者：J. S. Yadav、B. V. S. Reddy、Ch. Srinivas Reddy、K. Rajasekhar

  DOI：10.1246/cl.2004.476

  日期：2004.4

  Epoxides undergo rapid ring-opening with lithium halides in [bmim]PF6 or [bmim]BF4 ionic liquids under mild and neutral conditions to afford the corresponding vic-halohydrins in high to quantitative yields. The epoxides show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly. The recovered ionic liquid can be reused in three to four subsequent runs with consistent activity.

  在温和的中性条件下，环氧化物在 [bmim]PF6 或 [bmim]BF4 离子液体中与卤化锂发生快速开环反应，生成相应的沧卤素，产率高至定量。环氧化物在离子液体中显示出更强的反应性，从而缩短了反应时间并显著提高了产率。回收的离子液体可重复使用三至四次，且活性稳定。
• Ionic Liquid as Reagent. A Green Procedure for the Regioselective Conversion of Epoxides to <i>V</i><i>icinal</i>-Halohydrins Using [AcMIm]X under Catalyst- and Solvent-Free Conditions
  作者：Brindaban C. Ranu、Subhash Banerjee

  DOI：10.1021/jo0500885

  日期：2005.5.1

  A variety of structurally diverse epoxides undergo facile cleavages by ionic liquid, [AcMIm]X without any catalyst and solvent to produce the corresponding vicinal halohydrins in high yields. The cleavages are considerably fast and highly regioselective.
• Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin
  作者：M.Arjun Reddy、K Surendra、N Bhanumathi、K.Rama Rao

  DOI：10.1016/s0040-4020(02)00614-2

  日期：2002.7

  Highly regioselective ring opening of epoxides to halohydrins has been carried out in impressive yields with hydrogen and lithium halides in presence of beta-cyclodextrin using water as solvent. (C) 2002 Elsevier Science Ltd. All rights reserved.