(2S*)-2-{(3S*)-3-(tert-butyl-dimethylsilanyloxy)-pent-4-enyl}-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole

• 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: (2S*)-2-{(3S*)-3-(tert-butyl-dimethylsilanyloxy)-pent-4-enyl}-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole
• 英文别名: (+/-)-(2S)-2-{(3S)-3-(tert-butyldimethylsilanyloxy)-pent-4-enyl}-1-(toluene-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole；tert-butyl-[(3R)-5-[(2R)-4-ethenyl-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrol-2-yl]pent-1-en-3-yl]oxy-dimethylsilane
• 化学式: C₂₄H₃₇NO₃SSi
• 分子量: 447.714
• InChiKey: YCBRHNWDRIOMAI-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S*)-2-{(3S*)-3-(tert-butyl-dimethylsilanyloxy)-pent-4-enyl}-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole 在 四丁基氟化铵 作用下， 生成 (5aR*,8aR*,8bR*)-1-(toluene-4-sulfonyl)-2,4,5,5a,7,8,8a,8b-octahydro-1H-benzo[cd]indol-6-one
  参考文献：
  名称：

  钌催化的开环和闭环烯炔复分解。

  摘要：

  [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。

  DOI：

  10.1021/ol015606m
• 作为产物：
  描述：

  4-甲基-N-(丙-2-炔-1-基)苯-1-磺酰胺 在 Grubbs catalyst first generation 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 (2S*)-2-{(3S*)-3-(tert-butyl-dimethylsilanyloxy)-pent-4-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。
• ROM-RCM of cycloalkene-yne
  作者：Tsuyoshi Kitamura、Yuichi Kuzuba、Yoshihiro Sato、Hideaki Wakamatsu、Reiko Fujita、Miwako Mori

  DOI：10.1016/j.tet.2004.05.030

  日期：2004.8

  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.