1-(1H-indol-3-yl)-3-phenoxypropan-2-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(1H-indol-3-yl)-3-phenoxypropan-2-ol
• 英文别名: 1-(1H-indol-3-yl)-3-phenylpropan-2-ol；3-(3-indolyl)-1-phenoxy-2-propanol
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: NWNCCQAFTBHKLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 苯基缩水甘油醚 在 antimony trichloride/montmorillonite K-10 作用下， 反应 1.0h， 以58%的产率得到1-(1H-indol-3-yl)-3-phenoxypropan-2-ol
  参考文献：
  名称：

  三氯化锑/蒙脱土K-10催化的氮杂环的有效Friedel-Crafts烷基化

  摘要：

  已经发现，负载在蒙脱石K-10上的SbCl 3是有效的和可重复使用的催化剂，用于氮杂环化合物（如吲哚和吡咯）的Friedel-Crafts烷基化与环氧化物的反应。该反应以高区域选择性良好地获得优异产率的相应的C-烷基化衍生物。

  DOI：

  10.1016/j.tetlet.2008.12.022

文献信息

• An efficient Friedel–Crafts alkylation of nitrogen heterocycles catalyzed by antimony trichloride/montmorillonite K-10
  作者：Yu-Heng Liu、Qiu-Shuang Liu、Zhan-Hui Zhang

  DOI：10.1016/j.tetlet.2008.12.022

  日期：2009.2

  It has been found that SbCl3 supported on montmorillonite K-10 is an efficient and reusable catalyst for Friedel–Crafts alkylation of nitrogen heterocycles such as indoles and pyrroles with epoxides. The reaction gives the corresponding C-alkylated derivatives in good to excellent yields with a high regioselectivity.

  已经发现，负载在蒙脱石K-10上的SbCl 3是有效的和可重复使用的催化剂，用于氮杂环化合物（如吲哚和吡咯）的Friedel-Crafts烷基化与环氧化物的反应。该反应以高区域选择性良好地获得优异产率的相应的C-烷基化衍生物。
• Ultrasound-assisted regioselective ring opening of epoxides with nitrogen heterocycles using pyrrolidonium and imidazolium-based acidic ionic liquids
  作者：Masoumeh Zakeri、Mohamed Mahmoud Nasef、Ebrahim Abouzari-Lotf、Hoda Haghi

  DOI：10.1007/s11164-015-2015-4

  日期：2015.12

  Imidazolium and N-methyl-2-pyrrolidonium ionic liquids under ultrasound irradiation were developed as a green and expeditious approach for C--alkylation and N-alkylation of the nitrogen heterocycles including indoles and imidazoles with aliphatic and aromatic epoxides. Ionic liquids were used with a dual role of catalyst and solvent. The highest yield (85 %) was obtained with N-methyl-2-pyrrolidonium dihydrogen phosphate [H-NMP]H2PO4 as a pyrrolidonium ionic liquid under ultrasound at 50 kHz, with a reaction time of 60 min and reaction temperature of 60 °C. The combination of ionic liquids and ultrasonic irradiation was found to be an effective, green and eco-friendly method for alkylation of indoles and imidazoles.

  在超声辐射下，开发了咪唑鎓和N-甲基-2-吡咯烷鎓离子液体作为一种绿色快速的方法，用于氮杂环的C-烷基化和N-烷基化，包括吲哚和咪唑与脂肪族和芳香族环氧化物。离子液体在催化剂和溶剂中具有双重作用。在超声频率50 kHz、反应时间60分钟和反应温度60°C的条件下，使用N-甲基-2-吡咯烷鎓二氢磷酸盐[H-NMP]H2PO4作为吡咯烷鎓离子液体获得了最高产率（85%）。离子液体与超声辐射的结合被认为是一种有效、绿色且环保的方法，用于吲哚和咪唑的烷基化。
• InCl₃-Catalyzed Alkylation of Indoles with Epoxides
  作者：J. S. Yadav、B. V. Reddy、Sunny Abraham、G. Sabitha

  DOI：10.1055/s-2002-33532

  日期：——

  Indoles react smoothly with terminal epoxides in the presence of catalytic amount of InCl3 under mild conditions to afford the corresponding 3-alkyl indole derivatives in high yields with high regioselectivity.

  在温和的条件下，吲哚与末端环氧化物在催化量 InCl3 的存在下顺利发生反应，以高产率和高区域选择性得到相应的 3-烷基吲哚衍生物。
• Ultrasound assisted, ruthenium-exchanged FAU-Y zeolite catalyzed alkylation of indoles with epoxides under solvent free conditions
  作者：Alireza Khorshidi

  DOI：10.1016/j.ultsonch.2011.11.003

  日期：2012.5

  Ruthenium-exchanged FAU-Y zeolite (RuY) was used as a recyclable catalyst for regioselective ring-opening of epoxides with indoles under irradiation of sonic waves. It was found that a solvent free process, under the above mentioned conditions provides good yields of the desired 3-alkylated indole derivatives.

  钌交换的FAU-Y沸石（RuY）用作可再循环的催化剂，用于在声波辐射下用吲哚对环氧化合物进行区域选择性开环。发现在上述条件下的无溶剂方法提供了期望的3-烷基化的吲哚衍生物的良好产率。
• A simple, highly regioselective and efficient reaction of indole with epoxides under solvent-free conditions
  作者：Najmedin Azizi、Shokopheh Mehrazma、Mohammad R Saidi

  DOI：10.1139/v06-063

  日期：2006.5.1

  Lithium perchlorate has been found to be an inexpensive and efficient catalyst for the ring opening of epoxides by indole and N-methylindole, which provides an environmentally friendly method for the synthesis of substituted indoles. A complete regioselectivity in favor of nucleophilic attack at the benzylic carbon atom of aromatic epoxides, such as styrene oxide, is observed. However, aliphatic unsymmetrical alkene oxides undergo selective nucleophilic attack at the sterically less-hindered carbon atom. This catalyst offers several advantages, such as short reaction time, high yields, lower catalytic loading, simple experimental procedure, and easy isolation of the products, under solvent-free conditions.

  研究发现，高氯酸锂是吲哚和 N-甲基吲哚环氧化物开环的一种廉价而高效的催化剂，它为取代吲哚的合成提供了一种环境友好型方法。在芳香族环氧化物（如氧化苯乙烯）的苄基碳原子上进行亲核攻击时，可以观察到完全的区域选择性。然而，脂肪族非对称烯氧化物则会在立体阻碍较小的碳原子上发生选择性亲核反应。这种催化剂具有多种优点，如反应时间短、产率高、催化负载低、实验过程简单以及在无溶剂条件下易于分离产物。