N-(1,1-divinylhept-5-enyl)-2,2,2-trifluoro-N-(1-pentylbut-3-enyl)acetamide | 784201-70-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1,1-divinylhept-5-enyl)-2,2,2-trifluoro-N-(1-pentylbut-3-enyl)acetamide
• 英文别名: N-[(7Z)-3-ethenylnona-1,7-dien-3-yl]-2,2,2-trifluoro-N-non-1-en-4-ylacetamide
• CAS: 784201-70-3
• 化学式: C₂₂H₃₄F₃NO
• 分子量: 385.513
• InChiKey: BZXJRJNBXQJKBE-WDZFZDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  N-(1,1-divinylhept-5-enyl)-2,2,2-trifluoro-N-(1-pentylbut-3-enyl)acetamide 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 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：

  4-pent-4-enyl-4-vinyl-oxazolidin-2-one 在 sodium periodate 、 正丁基锂 、 AD-mix-β 、 三氟化硼乙醚 、 potassium tert-butylate 、 二异丁基氢化铝 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 49.16h， 生成 N-(1,1-divinylhept-5-enyl)-2,2,2-trifluoro-N-(1-pentylbut-3-enyl)acetamide
  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.