3-(4-hydroxybutyl)-2,4-dimethylcyclohex-2-enone | 872529-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-hydroxybutyl)-2,4-dimethylcyclohex-2-enone
• 英文别名: 3-(4-Hydroxybutyl)-2,4-dimethylcyclohex-2-en-1-one
• CAS: 872529-03-8
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: HGBYEHIGIHZHKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxybutyl)-2,4-dimethylcyclohex-2-enone 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以77%的产率得到4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butanal
  参考文献：
  名称：

  Study on the Base-Catalyzed Reverse Vinylogous Aldol Reaction of (4aβ,5β)-4,4a,5,6,7,8-Hexahydro- 5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one under Robinson Annulation Conditions

  摘要：

  We have proposed a pathway for the base-catalyzed reverse vinylogous aldol reaction of (-)-(4a beta,5 beta)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one [(-)-8] under Robinson annulation conditions. For confirmation, 4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butanal (11) and 4-(2,6-dimethyl-5-oxocyclohex-1-enyl)butanal (12), both of which potentially produce enolate 1, were synthesized regioselectively. Unexpectedly, 11 gave a complex mixture, including only a trace amount of (+/-)-8 (less than 5% yield), under these basic conditions. To the contrary, 12 cleanly afforded (+/-)-8 in 66% yield. This result provides evidence for our proposed mechanism of the above reaction.

  DOI：

  10.1021/jo0520036
• 作为产物：
  描述：

  4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butyric acid 在 盐酸 、 lithium aluminium tetrahydride 、 硫酸 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 3.5h， 生成 3-(4-hydroxybutyl)-2,4-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Study on the Base-Catalyzed Reverse Vinylogous Aldol Reaction of (4aβ,5β)-4,4a,5,6,7,8-Hexahydro- 5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one under Robinson Annulation Conditions

  摘要：

  We have proposed a pathway for the base-catalyzed reverse vinylogous aldol reaction of (-)-(4a beta,5 beta)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one [(-)-8] under Robinson annulation conditions. For confirmation, 4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butanal (11) and 4-(2,6-dimethyl-5-oxocyclohex-1-enyl)butanal (12), both of which potentially produce enolate 1, were synthesized regioselectively. Unexpectedly, 11 gave a complex mixture, including only a trace amount of (+/-)-8 (less than 5% yield), under these basic conditions. To the contrary, 12 cleanly afforded (+/-)-8 in 66% yield. This result provides evidence for our proposed mechanism of the above reaction.

  DOI：

  10.1021/jo0520036

文献信息

• Study on the Base-Catalyzed Reverse Vinylogous Aldol Reaction of (4aβ,5β)-4,4a,5,6,7,8-Hexahydro- 5-hydroxy-1,4a-dimethylnaphthalen-2(3<i>H</i>)-one under Robinson Annulation Conditions
  作者：Joshua N. Payette、Tadashi Honda、Hidenori Yoshizawa、Frank G. Favaloro、Gordon W. Gribble

  DOI：10.1021/jo0520036

  日期：2006.1.1

  We have proposed a pathway for the base-catalyzed reverse vinylogous aldol reaction of (-)-(4a beta,5 beta)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one [(-)-8] under Robinson annulation conditions. For confirmation, 4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butanal (11) and 4-(2,6-dimethyl-5-oxocyclohex-1-enyl)butanal (12), both of which potentially produce enolate 1, were synthesized regioselectively. Unexpectedly, 11 gave a complex mixture, including only a trace amount of (+/-)-8 (less than 5% yield), under these basic conditions. To the contrary, 12 cleanly afforded (+/-)-8 in 66% yield. This result provides evidence for our proposed mechanism of the above reaction.