2-hex-5-enyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole | 339541-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hex-5-enyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole
• 英文别名: 4-Ethenyl-2-hex-5-enyl-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole
• CAS: 339541-03-6
• 化学式: C₁₉H₂₅NO₂S
• 分子量: 331.479
• InChiKey: ROWNRWFOMWTDGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基烯丙基硅醚 、 2-hex-5-enyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到
  参考文献：
  名称：

  A Mechanism Switch in Enyne Metathesis Reactions Involving Rearrangement: Influence of Heteroatoms in the Propargylic Position

  摘要：

  Novel findings concerning the mechanism of enyne metathesis reactions involving rearrangement are presented. It has been demonstrated that the presence of either oxygen or nitrogen at the propargylic position leads to opposite regioselectivities in the presence of a cross-metathesis partner. The application of these reactions to domino processes is also described.

  DOI：

  10.1002/1615-4169(200208)344:6/7<631::aid-adsc631>3.0.co;2-w
• 作为产物：
  描述：

  N-环庚-2-烯-1-基-4-甲基苯磺酰胺 在 Grubbs catalyst first generation sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 2-hex-5-enyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  ROM-RCM of cycloalkene-yne

  摘要：

  Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of cycloalkene-yne was demonstrated using a first- or second-generation ruthenium complex. When cycloalkenes bearing the alkyne part at the C-3 position were reacted with a first-generation ruthenium-carbene complex under an atmosphere of ethylene, ROM-RCM proceeded smoothly to give skeletal reorganized products in good yields. In this reaction, cycloalkene-ynes having terminal alkyne were suitable. On the other hand, when cycloalkenes bearing the alkyne part at the C-1 position were treated with a second-generation ruthenium-carbene complex, ROM-RCM proceeded smoothly to give bicyclic compounds and/or dimeric compounds in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.030

文献信息

• Ruthenium-Catalyzed Ring-Opening and Ring-Closing Enyne Metathesis
  作者：Tsuyoshi Kitamura、Miwako Mori

  DOI：10.1021/ol015606m

  日期：2001.4.1

  a CH2Cl2 solution of an enyne containing the cycloalkene moiety was stirred in the presence of ruthenium-carbene complex (10 mol %) at room temperature under ethylene gas (1 atm), ring-opening and ring-closing metathesis occurred to afford cyclized triene. The reaction was carried out under argon gas, and no cyclized product was obtained. Enynes with a terminal alkyne gave good results.

  [反应：请参见文字]。当在室温下在乙烯气体（1个大气压）下于钌-卡宾配合物（10摩尔％）存在下搅拌含有环烯烃部分的烯炔的CH2Cl2溶液时，发生开环和闭环复分解反应，得到环化的三烯。该反应在氩气下进行，未获得环化产物。炔烃与末端炔烃的合成效果良好。