5,5-dimethyl-N-<1-2-(naphthylthio)ethenyl>-N-(phenylmethyl)-1-cyclopentene-1-carboxamide | 154222-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,5-dimethyl-N-<1-2-(naphthylthio)ethenyl>-N-(phenylmethyl)-1-cyclopentene-1-carboxamide
• 英文别名: N-benzyl-5,5-dimethyl-N-(1-naphthalen-2-ylsulfanylethenyl)cyclopentene-1-carboxamide
• CAS: 154222-65-8
• 化学式: C₂₇H₂₇NOS
• 分子量: 413.583
• InChiKey: JUWJUTNKTTZXAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-N-<1-2-(naphthylthio)ethenyl>-N-(phenylmethyl)-1-cyclopentene-1-carboxamide 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 1.5h， 生成 6,6-dimethyl-2-(phenylmethyl)-2-azaspiro<4.4>nonane
  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：

  2,2-二甲基环戊酮 在 吡啶 、 氢氧化钾 、 氯化亚砜 、 三乙胺 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 二乙二醇 、 苯 为溶剂， 反应 120.5h， 生成 5,5-dimethyl-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

• Photocyclization of Enamides. 38. Reductive Photocyclization of a-(Methylthio)- and a-(Arylthio)enamides
  作者：Takeaki Naito、Hiromi Tanada、Yumiko Suzuki、Haruko Saito、Toshiko Kiguchi、Ichiya Ninomiya

  DOI：10.3987/com-93-6465

  日期：——

  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.