1-(p-toluenesulfonyl)-5-vinyl-2,3-dihydro-1H-pyrrole | 406179-88-2

• 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: 1-(p-toluenesulfonyl)-5-vinyl-2,3-dihydro-1H-pyrrole
• 英文别名: 5-Ethenyl-1-(4-methylphenyl)sulfonyl-2,3-dihydropyrrole
• CAS: 406179-88-2
• 化学式: C₁₃H₁₅NO₂S
• 分子量: 249.334
• InChiKey: RSYJYSVCNFWHTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  N-苯基马来酰亚胺 、 1-(p-toluenesulfonyl)-5-vinyl-2,3-dihydro-1H-pyrrole 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以68%的产率得到(3aSR, 8aSR, 8bRS)-2-phenyl-6-(p-toluenesulfonyl)-4,6,7,8,8a,8b-hexahydro-3aH-2,6-diaza-as-indacene-1,3-dione
  参考文献：
  名称：

  Synthesis of cyclic dienamide using ruthenium-catalyzed ring-closing metathesis of ene–ynamide

  摘要：

  Ring-closing metathesis of ene-ynamide, which has alkene and ynamide moieties in a molecule, using a second-generation ruthenium carbene complex produced nitrogen-containing heterocycles, which have a dienamide moiety, in high yields. Diels-Alder reaction of the cyclized product with dienophile proceeded smoothly to give an indole or quinoline derivative in high yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.083
• 作为产物：
  描述：

  N-(but-3-enyl)-N-(2,2-dichlorovinyl)-p-toluenesulfonamide 在 正丁基锂 、 platinum(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 0.75h， 生成 1-(p-toluenesulfonyl)-5-vinyl-2,3-dihydro-1H-pyrrole
  参考文献：
  名称：

  酰胺的自由基级联环化和铂（II）催化的环异构化

  摘要：

  氰化物作为自由基和有机金属转变的新伙伴进行了测试。涉及5- exo - dig环化和6- endo - trig自由基捕获的自由基级联反应将酰胺转化为异多环化合物，例如异吲哚，异吲哚满酮和吡啶基-异吲哚满酮。各种烯基-甲苯磺酰基酰胺与氯化铂（II）反应并生成双环含氮杂环。这种空前的，易于操作的过程可以与一环转化中的中间体环状甲苯磺酰胺的水解反应结合在一起，从而提供环丁酮。

  DOI：

  10.1016/j.tet.2005.11.092

文献信息

• Radical cascade cyclizations and platinum(II)-catalyzed cycloisomerizations of ynamides
  作者：Frédéric Marion、Julien Coulomb、Aurore Servais、Christine Courillon、Louis Fensterbank、Max Malacria

  DOI：10.1016/j.tet.2005.11.092

  日期：2006.4

  Ynamides are tested as new partners in radical and organometallic transformations. A radical cascade involving a 5-exo-dig cyclization followed by a 6-endo-trig radical trapping transforms ynamides into hetero-polycyclic compounds such as isoindoles, isoindolinones and pyrido-isoindolones. Various ene–tosylynamides react with platinum(II) chloride and lead to bicyclic nitrogenated heterocycles. This

  氰化物作为自由基和有机金属转变的新伙伴进行了测试。涉及5- exo - dig环化和6- endo - trig自由基捕获的自由基级联反应将酰胺转化为异多环化合物，例如异吲哚，异吲哚满酮和吡啶基-异吲哚满酮。各种烯基-甲苯磺酰基酰胺与氯化铂（II）反应并生成双环含氮杂环。这种空前的，易于操作的过程可以与一环转化中的中间体环状甲苯磺酰胺的水解反应结合在一起，从而提供环丁酮。
• Platinum Dichloride-Catalyzed Cycloisomerization of Ene-ynamides
  作者：Frédéric Marion、Julien Coulomb、Christine Courillon、Louis Fensterbank、Max Malacria

  DOI：10.1021/ol049530g

  日期：2004.4.1

  [reaction: see text] Various ene-tosylynamides react with platinum(II) chloride and lead to bicyclic nitrogenated heterocycles. This unprecedented and easily operated process can be coupled with a hydrolysis of the intermediate cyclic tosylenamides in a one-pot transformation, which provides cyclobutanones.

  [反应：见正文]各种烯基甲苯磺酰胺与氯化铂（II）反应并生成双环含氮杂环。这种空前的，易于操作的过程可以与一环转化中的中间体环状甲苯磺酰胺的水解反应结合在一起，从而提供环丁酮。
• Synthesis of Cyclic Dienamide Using Ruthenium-Catalyzed Ring-Closing Metathesis of Ene-Ynamide
  作者：Nozomi Saito、Yukako Sato、Miwako Mori

  DOI：10.1021/ol017298y

  日期：2002.3.1

  [GRAPHICS]Ring-closing metathesis of ene-ynamide using the second-gene ration Grubbs' catalyst produced nitrogen-containing heterocycles, which have dienamide moieties, in high yields. Diels-Alder reaction of the cyclized product and dienophile proceeded smoothly to afford a bi- or tricyclic compound.
• Diastereoselective Gold-Catalyzed Cycloisomerizations of Ene-Ynamides
  作者：Sylvain Couty、Christophe Meyer、Janine Cossy

  DOI：10.1002/anie.200602270

  日期：2006.10.13
• Synthesis of different ring-size heterocycles from the same propargyl alcohol derivative by ligand effect on Pd(0)
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1016/s0040-4039(02)00043-6

  日期：2002.2

  The type of ligand oil in an allenylpalladium complex, which was prepared from propargyl alcohol derivative and Pd(0), plays an important role in determination of the ring size of the cyclized compound. An intermediary palladium complex bearing a monodentate ligand gave a cyclized compound via palladacycle, while that bearing a bidentate ligand gave one-carbon elongated cyclized compound via a eta(3)-propargylalladium complex. (C) 2002 Elsevier Science Ltd. All rights reserved.