N-<1-(2-naphthylthio)ethenyl>-N-(phenylmethyl)-1-cyclopentene-1-carboxamide | 136788-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-<1-(2-naphthylthio)ethenyl>-N-(phenylmethyl)-1-cyclopentene-1-carboxamide
• 英文别名: N-[1-(2-Naphthalenylthio)ethenyl]-N-(phenylmethyl)-1-cyclopentene-1-carboxamide；N-benzyl-N-(1-naphthalen-2-ylsulfanylethenyl)cyclopentene-1-carboxamide
• CAS: 136788-13-1
• 化学式: C₂₅H₂₃NOS
• 分子量: 385.53
• InChiKey: NIGZLJUJDUNWMI-UHFFFAOYSA-N

物化性质

• 沸点：
  616.8±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-<1-(2-naphthylthio)ethenyl>-N-(phenylmethyl)-1-cyclopentene-1-carboxamide 在 palladium hydroxide - carbon sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 25.0 ℃ 、182.38 kPa 条件下， 反应 17.5h， 生成 2-氮杂螺[4.4]壬烷
  参考文献：
  名称：

  Photocyclization of Enamides. 38. Reductive Photocyclization of a-(Methylthio)- and a-(Arylthio)enamides

  摘要：

  Reductive photocyclization of alpha-(methylthio)enamide (2) gave exclusively six-membered lactams (3) and (4) while the same reaction of alpha-(arylthio)enamides (6) and (12) was found to afford-five-membered lactams (7) and (13) as major products. A novel total synthesis of (+/-)-polyzonimine (18b) was accomplished by applying the newly found reductive photocyclization of alpha-(naphthylthio)enamide leading to the formation of five-membered lactams.

  DOI：

  10.3987/com-93-6465
• 作为产物：
  描述：

  2-羟基环戊基羧酸甲酯 在 吡啶 、 氢氧化钾 、 氯化亚砜 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 苯 为溶剂， 反应 15.5h， 生成 N-<1-(2-naphthylthio)ethenyl>-N-(phenylmethyl)-1-cyclopentene-1-carboxamide
  参考文献：
  名称：

  Photocyclization of Enamides. 38. Reductive Photocyclization of a-(Methylthio)- and a-(Arylthio)enamides

  摘要：

  Reductive photocyclization of alpha-(methylthio)enamide (2) gave exclusively six-membered lactams (3) and (4) while the same reaction of alpha-(arylthio)enamides (6) and (12) was found to afford-five-membered lactams (7) and (13) as major products. A novel total synthesis of (+/-)-polyzonimine (18b) was accomplished by applying the newly found reductive photocyclization of alpha-(naphthylthio)enamide leading to the formation of five-membered lactams.

  DOI：

  10.3987/com-93-6465

文献信息

• Reductive Photocyclization of a-Methylthio- and a-Arylthioenamides
  作者：Takeaki Naito、Hiromi Tanada、Toshiko Kiguchi、Ichiya Ninomiya

  DOI：10.3987/com-91-5766

  日期：——

  Reductive photocyclization of alpha -methylthio- and alpha -arylthioenamides (2a-c) gave six-membered lactams (3a-d) and five-membered lactams (4a,b).