2-(2-phenylcyclohept-1-en-1-yl)pyridine | 1298116-59-2

• 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: 2-(2-phenylcyclohept-1-en-1-yl)pyridine
• 英文别名: 2-(2-Phenylcyclohepten-1-yl)pyridine；2-(2-phenylcyclohepten-1-yl)pyridine
• CAS: 1298116-59-2
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: YUFZUOUHWRERJC-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68 °C
• 沸点：
  393.4±41.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(cyclohept-1-en-1-yl)pyridine 、 苯硼酸频哪醇酯 在 (2-methylpropyl)lithium 、 iron(III)-acetylacetonate 、 ZnBr₂*C₆H₁₆N₂ 、 顺-1,2-双(二苯基膦)乙烯 、 1,2-二氯-2-甲基丙烷 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 0.67h， 以72%的产率得到2-(2-phenylcyclohept-1-en-1-yl)pyridine
  参考文献：
  名称：

  Iron-Catalyzed C(sp²)–H Bond Functionalization with Organoboron Compounds

  摘要：

  We report here that an iron-catalyzed directed CH functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the CH bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.

  DOI：

  10.1021/ja5070763

文献信息

• Iron-Catalyzed Stereospecific Activation of Olefinic C–H Bonds with Grignard Reagent for Synthesis of Substituted Olefins
  作者：Laurean Ilies、Sobi Asako、Eiichi Nakamura

  DOI：10.1021/ja2017202

  日期：2011.5.25

  The reaction of an aryl Grignard reagent with a cyclic or acyclic olefin possessing a directing group such as pyridine or imine results in the stereospecific substitution of the olefinic C-H bond syn to the directing group. The reaction takes place smoothly and without isomerization of the product olefin in the presence of a mild oxidant (1,2-dichloro-2-methylpropane) and an aromatic cosolvent. Several

  芳基格氏试剂与具有导向基团（例如吡啶或亚胺）的环状或无环烯烃的反应导致烯属 CH 键顺式立体定向取代为导向基团。在温和氧化剂（1,2-二氯-2-甲基丙烷）和芳香族助溶剂的存在下，反应平稳进行且产物烯烃没有异构化。几条证据表明，该反应是通过铁催化的烯烃 CH 键活化而不是氧化性 Mizoroki-Heck 型反应进行的。
• Iron-Catalyzed C(sp²)–H Bond Functionalization with Organoboron Compounds
  作者：Rui Shang、Laurean Ilies、Sobi Asako、Eiichi Nakamura

  DOI：10.1021/ja5070763

  日期：2014.10.15

  We report here that an iron-catalyzed directed CH functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the CH bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.