2,2,2-trifluoro-1-(6-pent-4-enyl-2-pentyl-6-vinyl-3,6-dihydro-2H-pyridin-1-yl)ethanone | 784201-71-4

• 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: 2,2,2-trifluoro-1-(6-pent-4-enyl-2-pentyl-6-vinyl-3,6-dihydro-2H-pyridin-1-yl)ethanone
• 英文别名: 1-(6-Ethenyl-6-pent-4-enyl-2-pentyl-2,3-dihydropyridin-1-yl)-2,2,2-trifluoroethanone；1-(6-ethenyl-6-pent-4-enyl-2-pentyl-2,3-dihydropyridin-1-yl)-2,2,2-trifluoroethanone
• CAS: 784201-71-4
• 化学式: C₁₉H₂₈F₃NO
• 分子量: 343.433
• InChiKey: UVJWFIYDVVKXRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(6-pent-4-enyl-2-pentyl-6-vinyl-3,6-dihydro-2H-pyridin-1-yl)ethanone 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2,2,2-trifluoro-1-(2-pentyl-1-azaspiro[5.5]undeca-4,7-dien-1-yl)ethanone 、 2,2,2-trifluoro-1-(2-pentyl-1-azaspiro[5.5]undeca-4,7-dien-1-yl)ethanone
  参考文献：
  名称：

  A diastereoselective tandem RCM approach to spiropiperidines

  摘要：

  This paper outlines the stereocontrolled synthesis of a functionalised spiropiperidine through a diastereoselective tandem RCM reaction. The diastereoselectivity of this process was found to be strongly dependant on the nature of the catalyst; the less active first generation Ru-carbene complexes provided the desired spirocycle in high yield and with good stereocontrol. Additionally, the further functionalisation of the spiropiperidine was carried out through a regio- and stereoselective dihydroxylation reaction employing Donohoe's OsO4-TMEDA conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.025
• 作为产物：
  描述：

  2-(1-Allyl-hexylamino)-2-vinyl-hept-6-enal 在 Grubbs catalyst first generation potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 13.0h， 生成 2,2,2-trifluoro-1-(6-pent-4-enyl-2-pentyl-6-vinyl-3,6-dihydro-2H-pyridin-1-yl)ethanone
  参考文献：
  名称：

  A diastereoselective tandem RCM approach to spiropiperidines

  摘要：

  This paper outlines the stereocontrolled synthesis of a functionalised spiropiperidine through a diastereoselective tandem RCM reaction. The diastereoselectivity of this process was found to be strongly dependant on the nature of the catalyst; the less active first generation Ru-carbene complexes provided the desired spirocycle in high yield and with good stereocontrol. Additionally, the further functionalisation of the spiropiperidine was carried out through a regio- and stereoselective dihydroxylation reaction employing Donohoe's OsO4-TMEDA conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.025

文献信息

• A diastereoselective tandem RCM approach to spiropiperidines
  作者：Robert A.J. Wybrow、Andrew S. Edwards、Neil G. Stevenson、Harry Adams、Craig Johnstone、Joseph P.A. Harrity

  DOI：10.1016/j.tet.2004.07.025

  日期：2004.9

  This paper outlines the stereocontrolled synthesis of a functionalised spiropiperidine through a diastereoselective tandem RCM reaction. The diastereoselectivity of this process was found to be strongly dependant on the nature of the catalyst; the less active first generation Ru-carbene complexes provided the desired spirocycle in high yield and with good stereocontrol. Additionally, the further functionalisation of the spiropiperidine was carried out through a regio- and stereoselective dihydroxylation reaction employing Donohoe's OsO4-TMEDA conditions. (C) 2004 Elsevier Ltd. All rights reserved.