N-((3-(4-methylphenyl)-6-phthalimido)-hexanoyl)-8-aminoquinoline | 1215018-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((3-(4-methylphenyl)-6-phthalimido)-hexanoyl)-8-aminoquinoline
• 英文别名: 6-(1,3-dioxoisoindol-2-yl)-3-(4-methylphenyl)-N-quinolin-8-ylhexanamide
• CAS: 1215018-97-5
• 化学式: C₃₀H₂₇N₃O₃
• 分子量: 477.563
• InChiKey: PKYFOKWWYYUZLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-((3-(4-methylphenyl)-6-phthalimido)-hexanoyl)-8-aminoquinoline 在 Ni(TMHD)₂ 作用下， 反应 24.0h， 以78%的产率得到
  参考文献：
  名称：

  未活化的8-氨基喹啉酰胺的直接催化醇解

  摘要：

  未活化酰胺的直接催化醇解是有机化学中最困难的挑战之一，尚未报道可用于裂解用作区域选择性官能化反应中的导向基团的酰胺的方法。在本文中，我们报道了8-氨基喹啉酰胺的直接催化醇解，这是区域选择性功能化反应中的高效引导基团。反应以底物，空气稳定的催化剂和醇的简单组合进行，以高收率提供具有宽泛的官能团耐受性的相应酯。还介绍了在相关羰基官能团存在的情况下对8-氨基喹啉酰胺的高度化学选择性裂解，以及初步的机理研究。

  DOI：

  10.1021/acscatal.7b00442
• 作为产物：
  描述：

  4-碘甲苯 、 6-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)hexanamide 在 cesium phosphate 、 palladium diacetate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 25.0h， 以76%的产率得到N-((3-(4-methylphenyl)-6-phthalimido)-hexanoyl)-8-aminoquinoline
  参考文献：
  名称：

  Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds

  摘要：

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.

  DOI：

  10.1021/ja910900p

文献信息

• Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds
  作者：Dmitry Shabashov、Olafs Daugulis

  DOI：10.1021/ja910900p

  日期：2010.3.24

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.
• Direct Catalytic Alcoholysis of Unactivated 8-Aminoquinoline Amides
  作者：Toru Deguchi、Hai-Long Xin、Hiroyuki Morimoto、Takashi Ohshima

  DOI：10.1021/acscatal.7b00442

  日期：2017.5.5

  unactivated amides is one of the most difficult challenges in organic chemistry, and an applicable method for cleaving amides used as directing groups in regioselective functionalization reactions has not been reported. Herein, we report direct catalytic alcoholysis of 8-aminoquinoline amides, which are highly effective directing groups in regioselective functionalization reactions. The reactions proceeded

  未活化酰胺的直接催化醇解是有机化学中最困难的挑战之一，尚未报道可用于裂解用作区域选择性官能化反应中的导向基团的酰胺的方法。在本文中，我们报道了8-氨基喹啉酰胺的直接催化醇解，这是区域选择性功能化反应中的高效引导基团。反应以底物，空气稳定的催化剂和醇的简单组合进行，以高收率提供具有宽泛的官能团耐受性的相应酯。还介绍了在相关羰基官能团存在的情况下对8-氨基喹啉酰胺的高度化学选择性裂解，以及初步的机理研究。