(9ci)-5,5-二甲基-1-环戊烯-1-羰酰氯 | 154222-76-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 中文名称: (9ci)-5,5-二甲基-1-环戊烯-1-羰酰氯
• 英文名称: 5,5-dimethyl-1-cyclopentene-1-carbonyl chloride
• 英文别名: 1-Cyclopentene-1-carbonylchloride, 5,5-dimethyl-；5,5-dimethylcyclopentene-1-carbonyl chloride
• CAS: 154222-76-1
• 化学式: C₈H₁₁ClO
• 分子量: 158.628
• InChiKey: CZXKUFMOIQDMRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (9ci)-5,5-二甲基-1-环戊烯-1-羰酰氯 在 palladium hydroxide - carbon sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙腈 、 苯 为溶剂， 25.0 ℃ 、182.38 kPa 条件下， 反应 106.5h， 生成 9,9-Dimethyl-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 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 二乙二醇 、 苯 为溶剂， 反应 110.5h， 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

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.