5,5-dimethyl-1-cyclopentene-1-carbonitrile | 154222-74-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5,5-dimethyl-1-cyclopentene-1-carbonitrile
• 英文别名: 5,5-dimethylcyclopentene-1-carbonitrile
• CAS: 154222-74-9
• 化学式: C₈H₁₁N
• 分子量: 121.182
• InChiKey: GZOWQZBRHGNLQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-1-cyclopentene-1-carbonitrile 在 氢氧化钾 、 氯化亚砜 作用下， 以 二乙二醇 为溶剂， 反应 73.0h， 生成 (9ci)-5,5-二甲基-1-环戊烯-1-羰酰氯
  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 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 37.5h， 生成 5,5-dimethyl-1-cyclopentene-1-carbonitrile
  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.