(E)-5-(2,2-Bis-phenylsulfanyl-vinylamino)-pent-2-enoic acid ethyl ester | 221100-32-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-5-(2,2-Bis-phenylsulfanyl-vinylamino)-pent-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-5-[2,2-bis(phenylsulfanyl)ethenylamino]pent-2-enoate
• CAS: 221100-32-9
• 化学式: C₂₁H₂₃NO₂S₂
• 分子量: 385.551
• InChiKey: PHDXLZPYOVYSJD-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-5-(2,2-Bis-phenylsulfanyl-vinylamino)-pent-2-enoic acid ethyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 N,N-二乙基苯胺 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (E)-5-[1-(Bis-phenylsulfanyl-methyl)-6,7-dimethoxy-3-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective radical cascade approach to benzo[a]quinolizidines

  摘要：

  The treatment of enamide 15, having an (E)-4-ethoxycarbonyl-3-butenyl group on the nitrogen atom. with Bu3SnH-AIBN in boiling benzene, afforded a 1.2:1 mixture of two benzo[a] quinolizidine stereoisomers 16 and 17 as a result of cascade radical cyclization. A similar treatment of the (2)-4-ethoxycarbonyl-3-butenyl congener 19 gave 16 and 17 in a ratio of 3.4:1. The high stereoselectivity (16:17 = 37:1) from 19 was obtained using Et3B as the initiator at -78 degrees C in toluene. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02550-7
• 作为产物：
  描述：

  ethyl 5-[N-(tert-butoxycarbonyl)amino]-2-pentenoate 在 magnesium sulfate 、 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (E)-5-(2,2-Bis-phenylsulfanyl-vinylamino)-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective radical cascade approach to benzo[a]quinolizidines

  摘要：

  The treatment of enamide 15, having an (E)-4-ethoxycarbonyl-3-butenyl group on the nitrogen atom. with Bu3SnH-AIBN in boiling benzene, afforded a 1.2:1 mixture of two benzo[a] quinolizidine stereoisomers 16 and 17 as a result of cascade radical cyclization. A similar treatment of the (2)-4-ethoxycarbonyl-3-butenyl congener 19 gave 16 and 17 in a ratio of 3.4:1. The high stereoselectivity (16:17 = 37:1) from 19 was obtained using Et3B as the initiator at -78 degrees C in toluene. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02550-7