ethyl 3-[3-methyl-2-(pyridin-2-yl)phenyl]propanoate | 1099591-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 3-[3-methyl-2-(pyridin-2-yl)phenyl]propanoate
• 英文别名: ethyl 3-[2-(2-pyridyl)-3-methylphenyl]propionate
• CAS: 1099591-96-4
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: KCCXQYXITOWFFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-(邻甲苯)吡啶 、 potassium 3-trifluoroboratopropionate ethyl ester 在 manganese(III) fluoride 、 palladium diacetate 、 溶剂黄146 作用下， 以 2,2,2-三氟乙醇 、 水 为溶剂， 反应 6.0h， 以46%的产率得到ethyl 3-[3-methyl-2-(pyridin-2-yl)phenyl]propanoate
  参考文献：
  名称：

  Mild Palladium-Catalyzed C–H Alkylation Using Potassium Alkyltrifluoroborates in Combination with MnF₃

  摘要：

  A Pd-catalyzed method for ligand-directed C-H alkylation with organoboron reagents is described. The combination of potassium organo-trifluoroborates, MnF3, and a Pd-II catalyst effects pyridine and amide-directed C-H alkylation. These reactions proceed under mild conditions (25-40 degrees C in weakly acidic media), are effective for installing methyl and 1 degrees alkyl groups, and do not require promoters such as benzoquinone.

  DOI：

  10.1021/ol400888r

文献信息

• Reactions and Mechanistic Studies of Rhenium-Catalyzed Insertion of α,β-Unsaturated Carbonyl Compounds into a C–H Bond
  作者：Yoichiro Kuninobu、Yuta Nishina、Kayo Okaguchi、Makoto Shouho、Kazuhiko Takai

  DOI：10.1246/bcsj.81.1393

  日期：2008.11.15

  A rhenium complex, [ReBr(CO) 3 (thf)] 2 , catalyzes the insertion of α,β-unsaturated carbonyl compounds into a C-H bond of aromatic compounds having nitrogen-containing directing groups. In this reaction, Re 2 (CO) 10 can also be used as a catalyst. When imines are employed as the aromatic substrates, sequential cyclization proceeds and indene derivatives are obtained in good to excellent yields. This

  铼络合物[ReBr(CO) 3 (thf)] 2 催化α,β-不饱和羰基化合物插入具有含氮导向基团的芳族化合物的CH键中。在该反应中，Re 2 (CO) 10 也可用作催化剂。当使用亚胺作为芳族底物时，顺序环化进行，并以良好至极好的产率获得茚衍生物。这种反应性与钌和铑配合物的反应性相反，钌和铑配合物通常用作不饱和分子插入 CH 键的催化剂。对反应机理的研究表明，铼催化剂促进了芳香族化合物的 CH 键活化，α,β-不饱和羰基化合物插入 Re-C 键，
• Complete Switch of Selectivity in the C–H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups
  作者：Jiyu Kim、Sung-Woo Park、Mu-Hyun Baik、Sukbok Chang

  DOI：10.1021/jacs.5b09824

  日期：2015.10.28

  A complete switch in the Cp*Ir(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the beta-H elimination, which ultimately affords the observed chemoselectivity.