2-(1-pyridinium)-1-(o-tolyl)ethanone bromide | 23711-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-pyridinium)-1-(o-tolyl)ethanone bromide
• 英文别名: 1-(2-methyl-phenacyl)-pyridinium; bromide；1-(2-Methylphenyl)-2-pyridin-1-ium-1-ylethanone;bromide
• CAS: 23711-37-7
• 化学式: Br*C₁₄H₁₄NO
• 分子量: 292.175
• InChiKey: VMLHRGHCOOZEBI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-pyridinium)-1-(o-tolyl)ethanone bromide 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 6.0h， 以61%的产率得到1-(1-hydroxy-2-o-tolylethyl)pyridinium bromide
  参考文献：
  名称：

  Arai, Sadao; Yamazaki, Masuo; Hida, Mitsuhiko, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 4, p. 1073 - 1078

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基苯基乙酮 在 溴 作用下， 生成 2-(1-pyridinium)-1-(o-tolyl)ethanone bromide
  参考文献：
  名称：

  88.芳香族侧链反应的机理，特别涉及替代品的极性效应。第九部分 苯甲酰溴与吡啶反应中的邻位作用

  摘要：

  DOI：

  10.1039/jr9380000445

文献信息

• Facile one-pot tandem synthesis of perfluoroalkylated indolizines under metal-free mild conditions
  作者：Dong He、Yuhong Xu、Jing Han、Hongmei Deng、Min Shao、Jie Chen、Hui Zhang、Weiguo Cao

  DOI：10.1016/j.tet.2017.01.005

  日期：2017.2

  A direct metal-free method for the synthesis of perfluoroalkylated indolizines by means of DIPEA-promoted tandem CN/CC bond formation was developed. Various substituted pyridines and bromoacetyl derivatives with methyl perfluoroalk-2-ynoates proceeded smoothly in this mild transformation, and the desired products were obtained in good to excellent yields under air.

  开发了一种直接无金属的方法，该方法通过DIPEA促进的串联C N / C C键的形成来合成全氟烷基化的吲哚嗪。在这种温和的转化过程中，各种被全氟烷基-2-丙酮酸甲酯取代的吡啶和溴代乙酰基衍生物可顺利进行，并在空气中以良好或优异的收率获得所需的产物。
• 1,2-Dicarbofunctionalization of Trifluoromethyl Alkenes with Pyridinium Salts via a Cycloaddition/Visible-Light-Enabled Fragmentation Cascade
  作者：Shu-Jie Chen、Guo-Shu Chen、Tao Deng、Jia-Hui Li、Zhi-Qing He、Li-Shan Liu、Hai Ren、Yun-Lin Liu

  DOI：10.1021/acs.orglett.1c04148

  日期：2022.1.21

  Although trifluoromethyl alkenes have great synthetic potential, their 1,2-difunctionalization has been a challenge. In this Letter, we disclose the first 1,2-dicarbofunctionalization of trifluoromethyl alkenes with pyridinium salts via a cascade process involving a base-promoted [3 + 2] cycloaddition followed by a visible-light-mediated Norrish-type-II fragmentation. This protocol allows for the formation

  尽管三氟甲基烯烃具有巨大的合成潜力，但它们的 1,2-双官能化一直是一个挑战。在这封信中，我们公开了三氟甲基烯烃与吡啶鎓盐的第一个 1,2-二碳官能化反应，该反应通过一个级联过程进行，包括碱促进的 [3 + 2] 环加成，然后是可见光介导的 Norrish-II 型片段化。该协议允许在温和条件下以中等至优异的产率形成带有三氟甲基取代的季铵中心的吡啶。
• Chiral “Metallo-Spiralenes”: Helical Molecules Conformationally Stabilised by an Organometallic Scaffold
  作者：Jean-Pierre Djukic、Christophe Michon、Aline Maisse-François、Rouben Allagapen、Michel Pfeffer、Karl Heinz Dötz、André De Cian、Jean Fischer

  DOI：10.1002/(sici)1521-3765(20000317)6:6<1064::aid-chem1064>3.0.co;2-g

  日期：2000.3.17

  The synthesis of a series of chiral cylomanganated 2-[(eta(6)-phenyl)Cr(CO)(3)]pyridine complexes derived from (-)-beta-pinene enables, by a "spirogenic transformation", the preparation of four different chiral helical heterobimetallic syn-facial complexes or Cr-0/Mn-1-spiralenes. among which two possess a right-handed P molecular helicity and two other a left-handed M one. These organometallic helical molecules are synthesised by applying two different methods to the chiral cyclomanganated (eta 6-arene)tricarbonylchromium substrates. The first method is the so-called "Fischer route" which involves a sequential addition of PhLi and MeOTf. The second method based on reaction of the cyclomanganated complex with diphenyldiazomethane which has been tested on achiral bimetallic substrates is a reasonable neutral alternative to the "Fischer methodology" for the synthesis of Cr-0/Mn-1-spiralenes. The crystal structure of one of these heterobimetallic chiral helical compounds serves as a starting point in the configurational and structural assessment of the synthesised chiral (eta(6)-arene)tricarbonylchromium complexes. Application of the "Fischer route" to a cyclomanganated chiral 2-phenylpyridine generates a single chiral eta(3)-benzylic complex-or Mn-1-spiralene-bearing a left-handed M helicity which has been characterized by X-ray diffraction analysis. Circular dichroic spectroscopic measurements underline the predominant contribution of the chiral and chirally induced aromatic chromophores to the sign of the Cotton effects and confirm the helical configurations of the considered heterobimetallic species.
• ARAI, SADAO;YAMAZAKI, MASUO;HIDA, MITSUHIKO, J. HETEROCYCL. CHEM., 27,(1990) N, C. 1073-1078
  作者：ARAI, SADAO、YAMAZAKI, MASUO、HIDA, MITSUHIKO

  DOI：——

  日期：——
• 88. Mechanism of aromatic side-chain reactions with special reference to the polar effects of substituents. Part IX. The ortho-effect in the reaction of phenacyl bromides with pyridine
  作者：John W. Baker

  DOI：10.1039/jr9380000445

  日期：——