2,2-dimethylpropanoic acid 4-(2-quinolinyl)phenyl ester | 634613-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,2-dimethylpropanoic acid 4-(2-quinolinyl)phenyl ester
• 英文别名: Propanoic acid, 2,2-dimethyl-, 4-(2-quinolinyl)phenyl ester；(4-quinolin-2-ylphenyl) 2,2-dimethylpropanoate
• CAS: 634613-69-7
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: BFQMFVHUJMFYFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-5-硝基苯甲醛 、 2,2-dimethylpropanoic acid 4-(2-quinolinyl)phenyl ester 在 [Cp*Rh(CH₃CN)₃](BF₄)₂ 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 24.0h， 以79%的产率得到3-((2-chloro-5-nitrophenyl)(hydroxy)methyl)-4-(quinolin-2-yl)phenyl pivalate
  参考文献：
  名称：

  N-Directing Group Assisted Rhodium-Catalyzed Aryl C–H Addition to Aryl Aldehydes

  摘要：

  Direct aryl C-H addition to aryl aldehydes to produce biaryl methanols was reported via Rh catalysis with an N-containing directing group. The method is highly atom-, step-, and redox-economic. The procedure is robust, reliable, and compatible with water and air.

  DOI：

  10.1021/ol2032784
• 作为产物：
  描述：

  2-氯喹啉 、 4-iodophenyl pivalate 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 以74%的产率得到2,2-dimethylpropanoic acid 4-(2-quinolinyl)phenyl ester
  参考文献：
  名称：

  杂环氯化物与芳基和杂芳基卤化镁的新型钴催化交叉偶联反应

  摘要：

  芳基镁卤化物和 2-氯吡啶和相关杂环之间的新钴催化交叉偶联发生在低温下，导致 2-芳基化杂环的产率很高。

  DOI：

  10.1055/s-2003-41460

文献信息

• Aromatic C-H Addition to Ketones: The Effect of Directing Groups
  作者：Xi-Sha Zhang、Qi-Lei Zhu、Fei-Xian Luo、Guihua Chen、Xin Wang、Zhang-Jie Shi

  DOI：10.1002/ejoc.201301115

  日期：2013.10

  The first example of the transition-metal-catalyzed direct intermolecular C–H bond addition to ketones was achieved by using a rhodium catalyst. A significant influence of the directing group on the reactivity was observed, and sterically more hindered directing groups could promote the reaction. In addition, intermolecular hydrogen bonding played a role in stabilizing the product. The substrate scope

  通过使用铑催化剂实现了过渡金属催化的直接分子间 C-H 键加成到酮的第一个例子。观察到导向基团对反应性的显着影响，空间位阻更大的导向基团可以促进反应。此外，分子间氢键在稳定产物方面发挥了作用。喹啉衍生物的底物范围非常好。
• New Cobalt-Catalyzed Cross-Coupling Reactions of Heterocyclic Chlorides with Aryl and Heteroaryl Magnesium Halides
  作者：Paul Knochel、Tobias J. Korn、Gérard Cahiez

  DOI：10.1055/s-2003-41460

  日期：——

  New cobalt-catalyzed cross-coupling between arylmagnesium halides and 2-chloropyridines and related heterocycles occur at low temperature leading to 2-arylated heterocycles in good yields.

  芳基镁卤化物和 2-氯吡啶和相关杂环之间的新钴催化交叉偶联发生在低温下，导致 2-芳基化杂环的产率很高。
• <i>N</i>-Directing Group Assisted Rhodium-Catalyzed Aryl C–H Addition to Aryl Aldehydes
  作者：Yang Li、Xi-Sha Zhang、Kang Chen、Ke-Han He、Fei Pan、Bi-Jie Li、Zhang-Jie Shi

  DOI：10.1021/ol2032784

  日期：2012.1.20

  Direct aryl C-H addition to aryl aldehydes to produce biaryl methanols was reported via Rh catalysis with an N-containing directing group. The method is highly atom-, step-, and redox-economic. The procedure is robust, reliable, and compatible with water and air.
• Cobalt-Catalyzed Cross-Coupling Reactions of Heterocyclic Chlorides with Arylmagnesium Halides and of Polyfunctionalized Arylcopper Reagents with Aryl Bromides, Chlorides, Fluorides and Tosylates
  作者：Paul Knochel、Tobias Korn、Matthias Schade、Murthy Cheemala、Stefan Wirth、Simon Guevara、Gérard Cahiez

  DOI：10.1055/s-2006-950290

  日期：2006.11

  A range of aromatic organocopper or organomagnesium compounds undergo smooth cross-coupling reactions with aryl bromides, chlorides, fluorides and tosylates, leading to polyfunctionalized aromatics or heterocycles in the presence of cobalt salts (5-7.5 mol%) as catalysts. Very mild reaction conditions are needed and, in the case of cross-coupling with organocopper compounds, Bu4NI (1 equiv) and 4-fluorostyrene (20 mol%) are essential as promoters for successful couplings.

  一系列芳香族有机铜或有机镁化合物与芳基溴、氯、氟及托烯磺酸酯进行平滑的交叉偶联反应，在钴盐（5-7.5 mol%）作为催化剂的情况下，产生多功能化的芳香族化合物或杂环化合物。反应条件非常温和，且在与有机铜化合物交叉偶联的情况下，四丁基氮化铵（1当量）和4-氟苯乙烯（20 mol%）是成功偶联所必需的促进剂。