ethyl (1S,2R,3R,10bS)-1-cyano-2-[(R)-(4-methylphenyl)sulfinyl]-1,2,3,10b-tetrahydropyrrolo[2,1-a]isoquinoline-3-carboxylate | 1283761-10-3

• 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: ethyl (1S,2R,3R,10bS)-1-cyano-2-[(R)-(4-methylphenyl)sulfinyl]-1,2,3,10b-tetrahydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• CAS: 1283761-10-3
• 化学式: C₂₃H₂₂N₂O₃S
• 分子量: 406.505
• InChiKey: PDSGBZLDPUVQKS-PAFDTYDNSA-N

物化性质

• 沸点：
  654.3±55.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(乙氧羰基甲基)-6-甲氧基喹啉鎓 、 (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile 以 乙腈 为溶剂， 反应 0.08h， 以81%的产率得到ethyl (1S,2R,3S,10bR)-1-cyano-2-[(R)-(4-methylphenyl)sulfinyl]-1,2,3,10b-tetrahydropyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinoline Derivatives by 1,3-Dipolar Cycloadditions of Stabilized IsoquinoliniumN-Ylides with Sulfinyl Dipolarophiles

  摘要：

  Enantiomerically pure pyrrolo[2,1-a]isoquinoline derivatives are obtained by 1,3-dipolar reactions of isoquinolinium azomethine ylides with enantiopure 3-p-tolylsulfinylacrylonitriles, tert-butyl (2E)-4,4-diethoxy-2-p-tolylsulfinylbut-2-enoate, and 5-ethoxy-3-p-tolylsulfinylfuran-2(5H)-ones. Reactions evolve through the anti conformation of the ylide with complete regioselectivity. The facial selectivity is completely controlled by the configuration of the sulfinyl sulfur for acyclic dipolarophiles, whereas it is high (dr 83/17 or 89/11) but controlled by the C-5 configuration for sulfinylfuranones. Complete endo selectivity is observed with cyclic dipolarophiles and substituted acrylonitriles, but it is low with butenoate. The sulfinyl group also exerts a positive influence on the dipolarophilic reactivity toward these ylides.

  DOI：

  10.1021/jo200191c

文献信息

• Asymmetric Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinoline Derivatives by 1,3-Dipolar Cycloadditions of Stabilized Isoquinolinium<i>N</i>-Ylides with Sulfinyl Dipolarophiles
  作者：José Luis García Ruano、Alberto Fraile、M. Rosario Martín、Gemma González、Cristina Fajardo、Ana María Martín-Castro

  DOI：10.1021/jo200191c

  日期：2011.5.6

  Enantiomerically pure pyrrolo[2,1-a]isoquinoline derivatives are obtained by 1,3-dipolar reactions of isoquinolinium azomethine ylides with enantiopure 3-p-tolylsulfinylacrylonitriles, tert-butyl (2E)-4,4-diethoxy-2-p-tolylsulfinylbut-2-enoate, and 5-ethoxy-3-p-tolylsulfinylfuran-2(5H)-ones. Reactions evolve through the anti conformation of the ylide with complete regioselectivity. The facial selectivity is completely controlled by the configuration of the sulfinyl sulfur for acyclic dipolarophiles, whereas it is high (dr 83/17 or 89/11) but controlled by the C-5 configuration for sulfinylfuranones. Complete endo selectivity is observed with cyclic dipolarophiles and substituted acrylonitriles, but it is low with butenoate. The sulfinyl group also exerts a positive influence on the dipolarophilic reactivity toward these ylides.