2-(1-chloro-2-phenylethyl)pyridine | 97026-56-7

• 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-(1-chloro-2-phenylethyl)pyridine
• 英文别名: 2-<1-Chlor-2-phenyl-ethyl>-pyridin；2-(α-chloro-phenethyl)-pyridine；2-(α-Chlor-phenaethyl)-pyridin
• CAS: 97026-56-7
• 化学式: C₁₃H₁₂ClN
• 分子量: 217.698
• InChiKey: LKLLKRYGBOHRGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-[(E)-2-phenylethenyl]pyridine 在 盐酸 、 臭氧 作用下， 生成 2-(1-chloro-2-phenylethyl)pyridine
  参考文献：
  名称：

  Harries; Lenart, Justus Liebigs Annalen der Chemie, 1915, vol. 410, p. 111

  摘要：

  DOI：

文献信息

• A Modular Dual‐Catalytic Aryl‐Chlorination of Alkenes
  作者：Bo Li、Ala Bunescu、Daniel Drazen、Katherine Rolph、Jean Michalland、Matthew J. Gaunt

  DOI：10.1002/anie.202405939

  日期：2024.8.19

  Alkyl chlorides are a class of versatile building blocks widely used to generate C(sp3)‐rich scaffolds through transformation such as nucleophilic substitution, radical addition reactions and metal‐catalyzed cross‐coupling processes. Despite their utility in the synthesis of high‐value functional molecules, distinct methods for the preparation of alkyl chlorides are underrepresented. Here, we report a visible‐light‐mediated dual catalysis strategy for the modular synthesis of highly functionalized and structurally diverse arylated chloroalkanes via the coupling of diaryliodonium salts, alkenes and potassium chloride. A distinctive aspect of this transformation is a ligand‐design‐driven approach for the development of a copper(II)‐based atom‐transfer catalyst that enables the aryl‐chlorination of electron‐poor alkenes, complementing its iron(III)‐based counterpart that accommodates non‐activated aliphatic alkenes and styrene derivatives. The complementarity of the two dual catalytic systems allows the efficient aryl‐chlorination of alkenes bearing different stereo‐electronic properties and a broad range of functional groups, maximizing the structural diversity of the 1‐aryl, 2‐chloroalkane products.