4-butyl-2-phenyltetrahydro-2H-pyran | 1160592-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-butyl-2-phenyltetrahydro-2H-pyran
• 英文别名: 4-Butyltetrahydro-2-phenyl-2H-pyran；4-butyl-2-phenyloxane
• CAS: 1160592-01-7
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: WEOGLEIFWLEKJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-溴-2-苯基四氢-2H-吡喃 、 正丁基氯化镁 在 nickamine 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 2.5h， 以88%的产率得到4-butyl-2-phenyltetrahydro-2H-pyran
  参考文献：
  名称：

  Nickel-Catalyzed Diastereoselective Alkyl–Alkyl Kumada Coupling Reactions

  摘要：

  A nickel pincer complex is found to catalyze alkyl-alkyl Kumada coupling reactions of 1,3- and 1,4-substituted cyclohexyl halides and tetrahydropyrans with an excellent diastereoselectivity. The mechanistic investigation of the coupling reactions provides evidence that the activation of alkyl halides is reversible.

  DOI：

  10.1021/ol302067b

文献信息

• Vechorkin, Oleg; Hu, Xile, Angewandte Chemie - International Edition, 2009, vol. 48, p. 2937 - 2940
  作者：Vechorkin, Oleg、Hu, Xile

  DOI：——

  日期：——
• From Dimethylamine to Pyrrolidine: The Development of an Improved Nickel Pincer Complex for Cross-Coupling of Nonactivated Secondary Alkyl Halides
  作者：Pablo M. Perez Garcia、Thomas Di Franco、Alexandre Epenoy、Rosario Scopelliti、Xile Hu

  DOI：10.1021/acscatal.5b02324

  日期：2016.1.4

  Replacement of a dimethyl amino group of the amidobis(amine) nickel(II) pincer complex (1), [((N2N)-N-Me)-Ni-Cl], by a pyrrolidino group resulted in a new nickel(II) pincer complex (2), [((PNNN)-N-yr-N-Me)Ni-Cl]. Complex 2 is an efficient catalyst for Kumada and Suzuki-Miyaura cross-coupling of nonactivated secondary alkyl halides, while complex 1 is largely inactive. The significant activity difference is tentatively attributed to a minimal structural difference, which leads to a more hemilabile ligand.