4-pent-4-enyl-3-(1-pentylbut-3-enyl)-4-vinyloxazolidin-2-one | 667869-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-pent-4-enyl-3-(1-pentylbut-3-enyl)-4-vinyloxazolidin-2-one
• 英文别名: 4-Ethenyl-3-non-1-en-4-yl-4-pent-4-enyl-1,3-oxazolidin-2-one
• CAS: 667869-75-2
• 化学式: C₁₉H₃₁NO₂
• 分子量: 305.461
• InChiKey: AXHWDFCKAWFJTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-pent-4-enyl-3-(1-pentylbut-3-enyl)-4-vinyloxazolidin-2-one 在 Grubbs catalyst first generation potassium tert-butylate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 30.5h， 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
• 作为产物：
  描述：

  3-(1-Hydroxy-hexyl)-4-pent-4-enyl-4-vinyl-oxazolidin-2-one 在 2,6-二甲基吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 4-pent-4-enyl-3-(1-pentylbut-3-enyl)-4-vinyloxazolidin-2-one
  参考文献：
  名称：

  非对映选择性串联闭环复分解反应合成功能化螺环哌啶的研究

  摘要：

  报道了通过非对映选择性串联闭环复分解 (RCM) 反应立体选择性合成螺哌啶。发现立体化学从戊基链到三个碳原子外新形成的螺心的有效中继特别依赖于所用 Ru 催化剂的性质 - 发现第一代 Grubbs 催化剂比更活跃的第二代催化剂具有更高的选择性生成卡宾配合物。

  DOI：

  10.1055/s-2003-43366

文献信息

• Investigation of Diastereoselective Tandem Ring Closing Metathesis Reactions Toward the Synthesis of Functionalised Spirocyclic Piperidines
  作者：Joseph P. Harrity、Robert A. Wybrow、Neil G. Stevenson

  DOI：10.1055/s-2003-43366

  日期：——

  The stereoselective synthesis of a spiropiperidine through a diastereoselective tandem ring closing metathesis (RCM) reaction is reported. The efficient relay of stereochemistry from a pentyl chain to the newly formed spirocentre three carbon atoms away was found to be particularly dependant on the nature of the Ru-catalyst employed - 1st generation Grubbs catalyst was found to be significantly more

  报道了通过非对映选择性串联闭环复分解 (RCM) 反应立体选择性合成螺哌啶。发现立体化学从戊基链到三个碳原子外新形成的螺心的有效中继特别依赖于所用 Ru 催化剂的性质 - 发现第一代 Grubbs 催化剂比更活跃的第二代催化剂具有更高的选择性生成卡宾配合物。
• 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.