1-(2-氨基-3-甲氧基苯基)-2,2,2-三氟乙酮 | 489429-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-氨基-3-甲氧基苯基)-2,2,2-三氟乙酮
• 英文名称: 1-(2-amino-3-methoxyphenyl)-2,2,2-trifluoroethanone
• CAS: 489429-72-3
• 化学式: C₉H₈F₃NO₂
• 分子量: 219.163
• InChiKey: XIRKNTLEMGPMBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-戊酮 、 1-(2-氨基-3-甲氧基苯基)-2,2,2-三氟乙酮 在 potassium L-prolinate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.75h， 以90%的产率得到8-methoxy-2-propyl-4-(trifluoromethyl)quinoline
  参考文献：
  名称：

  脯氨酸钾盐：一种通过弗里德兰德法（Friedlander annulation）合成4-三氟甲基喹啉衍生物的优良催化剂

  摘要：

  脯氨酸钾盐首先成功地用于催化弗里德兰德环化反应，在温和的条件下以良好或优异的收率由取代的2-三氟乙酰基苯胺和各种羰基化合物合成4-三氟甲基取代的喹啉。该催化剂具有许多优点，例如反应时间短，区域选择性高，官能团耐受性强和底物范围广。

  DOI：

  10.1016/j.tet.2013.06.017
• 作为产物：
  描述：

  在 盐酸 、 水 、 sodium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 1-(2-氨基-3-甲氧基苯基)-2,2,2-三氟乙酮
  参考文献：
  名称：

  An alternative route for synthesis of o-trifluoroacetylanilines as useful fluorine-containing intermediates

  摘要：

  A series of o-trifluoroacetyl aniline derivatives were synthesized in three steps. In this method, we first utilized trifluoroacetic anhydride to introduce trifluoroacetyl group to the ortho position of aniline with higher yield than that of some previously reported methods. In addition, the procedure is shown to be highly regiospecific. This type of compounds can be used as the key intermediates in the preparation of a variety of inhibitors of HIV reverse transcriptase which is an important pharmacological target of many anti-AIDS agents. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.04.002

文献信息

• The First Proline-Catalyzed Friedlander Annulation: Regioselective Synthesis of 2-Substituted Quinoline Derivatives
  作者：Biao Jiang、Jia-jia Dong、Yun Jin、Xiao-long Du、Min Xu

  DOI：10.1002/ejoc.200800121

  日期：2008.6

  The first proline-catalyzed Friedlander annulation for the synthesis of 2-substituted 4-trifluoromethyl quinoline derivatives is described. Excellent re gio selectivity as well as good yields were shown in a variety of cases, and a tandem aldol-cyclization pathway might be involved. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

  描述了第一个用于合成 2-取代 4-三氟甲基喹啉衍生物的脯氨酸催化 Friedlander 环化。在各种情况下都显示出优异的区域选择性和良好的产率，并且可能涉及串联醛醇环化途径。((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)。
• Switchable Selectivity in the Annulation of <i>o</i>‐Trifluoroacetylanilines and Activated Terminal Alkynes Based on Transition Metal and Phosphine Catalysis
  作者：Alexander Yu. Mitrofanov、Arina V. Murashkina、Konstantin A. Lyssenko、Irina P. Beletskaya

  DOI：10.1002/chem.202302357

  日期：2023.11.16

  Based on Cu ang Ag catalysis as well as phosphine catalysis, we have developed efficient methods for the synthesis of three different types of CF3-substituted compounds (quinoline-3-carboxylates, quinoline-2-carboxylates, and indolines) from the same starting materials such as o-trifluoroacetylanilines and propiolates.

  基于Cu和Ag催化以及膦催化，我们开发了从同一起始点合成三种不同类型的CF 3取代化合物（喹啉-3-羧酸盐、喹啉-2-羧酸盐和二氢吲哚）的有效方法材料例如邻三氟乙酰苯胺和丙炔酸盐。
• Zn(II)-Mediated Alkynylation−Cyclization of <i>o</i>-Trifluoroacetyl Anilines:  One-Pot Synthesis of 4-Trifluoromethyl-Substituted Quinoline Derivatives
  作者：Biao Jiang、Yu-Gui Si

  DOI：10.1021/jo0204606

  日期：2002.12.1

  A novel efficient route to 4-trifluoromethyl-substituted quinoline derivatives through the Zn(II)-mediated alkynylation-cyclization of o-trifluoroacetyl anilines is described.
• Proline potassium salt: a superior catalyst to synthesize 4-trifluoromethyl quinoline derivatives via Friedlander annulation
  作者：Xiao Long Du、Biao Jiang、Yuan Chao Li

  DOI：10.1016/j.tet.2013.06.017

  日期：2013.9

  Proline potassium salt was successfully firstly used to catalyze the Friedlander annulation toward the synthesis of 4-trifluoromethyl-substituted quinolines from the substituted 2-trifluoroacetyl anilines and variety carbonyl compounds under mild conditions in good to excellent yields. This catalyst provides several advantages, such as shorter reaction time, high regioselectivity, functional group

  脯氨酸钾盐首先成功地用于催化弗里德兰德环化反应，在温和的条件下以良好或优异的收率由取代的2-三氟乙酰基苯胺和各种羰基化合物合成4-三氟甲基取代的喹啉。该催化剂具有许多优点，例如反应时间短，区域选择性高，官能团耐受性强和底物范围广。
• An alternative route for synthesis of o-trifluoroacetylanilines as useful fluorine-containing intermediates
  作者：Lingjian Zhu、Zhenyuan Miao、Chunquan Sheng、Jianzhong Yao、Chunlin Zhuang、Wannian Zhang

  DOI：10.1016/j.jfluchem.2010.04.002

  日期：2010.7

  A series of o-trifluoroacetyl aniline derivatives were synthesized in three steps. In this method, we first utilized trifluoroacetic anhydride to introduce trifluoroacetyl group to the ortho position of aniline with higher yield than that of some previously reported methods. In addition, the procedure is shown to be highly regiospecific. This type of compounds can be used as the key intermediates in the preparation of a variety of inhibitors of HIV reverse transcriptase which is an important pharmacological target of many anti-AIDS agents. (C) 2010 Elsevier B.V. All rights reserved.