3-N-[4'-(4'-chlorophenoxy)but-2'-ynyl],N-methylamino-5,5-dimethylcyclohex-2-enone | 358680-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-N-[4'-(4'-chlorophenoxy)but-2'-ynyl],N-methylamino-5,5-dimethylcyclohex-2-enone
• 英文别名: 3-[4-(4-Chlorophenoxy)but-2-ynyl-methylamino]-5,5-dimethylcyclohex-2-en-1-one；3-[4-(4-chlorophenoxy)but-2-ynyl-methylamino]-5,5-dimethylcyclohex-2-en-1-one
• CAS: 358680-14-5
• 化学式: C₁₉H₂₂ClNO₂
• 分子量: 331.842
• InChiKey: VLFMLBFAEBYTNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-N-[4'-(4'-chlorophenoxy)but-2'-ynyl],N-methylamino-5,5-dimethylcyclohex-2-enone 以 氯苯 为溶剂， 反应 12.0h， 以75%的产率得到7,7-dimethyl-1,2,3,6,7,8-hexahydro-4-(4'-chlorophenoxy)methylene-1-methylquinoline-5-one
  参考文献：
  名称：

  Studies in aza-Claisen rearrangement: synthesis of dimedone-annelated unusual heterocycles

  摘要：

  A number of 3-N-(4'-aryloxybut-2'-ynyl)N-methyl amino-5,5-dimethyl cyclohex-2-enones are synthesized in 62-65% yield by refluxing 3-chloro-5,5-dimethyl cyclohex-2-enone with a number of 4-aryloxy-4-chlorobut-2-ynes in ethanol for 4 h. The amines are then heated in refluxing chlorobenzene to give 7,7-dimethyl-1,2,3,6,7,8-hexahydro-4-aryloxymethylene-1-methyl quinoiine-5-one in 75-80% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00405-7
• 作为产物：
  描述：

  1-(4-chlorophenyl)oxy-4-chloro-but-2-yne 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 3-N-[4'-(4'-chlorophenoxy)but-2'-ynyl],N-methylamino-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Studies in aza-Claisen rearrangement: synthesis of dimedone-annelated unusual heterocycles

  摘要：

  A number of 3-N-(4'-aryloxybut-2'-ynyl)N-methyl amino-5,5-dimethyl cyclohex-2-enones are synthesized in 62-65% yield by refluxing 3-chloro-5,5-dimethyl cyclohex-2-enone with a number of 4-aryloxy-4-chlorobut-2-ynes in ethanol for 4 h. The amines are then heated in refluxing chlorobenzene to give 7,7-dimethyl-1,2,3,6,7,8-hexahydro-4-aryloxymethylene-1-methyl quinoiine-5-one in 75-80% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00405-7

文献信息

• Studies in aza-Claisen rearrangement: synthesis of dimedone-annelated unusual heterocycles
  作者：K.C. Majumdar、S.K. Samanta

  DOI：10.1016/s0040-4020(01)00405-7

  日期：2001.6

  A number of 3-N-(4'-aryloxybut-2'-ynyl)N-methyl amino-5,5-dimethyl cyclohex-2-enones are synthesized in 62-65% yield by refluxing 3-chloro-5,5-dimethyl cyclohex-2-enone with a number of 4-aryloxy-4-chlorobut-2-ynes in ethanol for 4 h. The amines are then heated in refluxing chlorobenzene to give 7,7-dimethyl-1,2,3,6,7,8-hexahydro-4-aryloxymethylene-1-methyl quinoiine-5-one in 75-80% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.