4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butyric acid | 71988-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butyric acid
• 英文别名: 4-(2,6-Dimethyl-3-oxocyclohexen-1-yl)butanoic acid
• CAS: 71988-47-1
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: CDDAZMWVLROSGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butyric acid 在 硫酸 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.75h， 生成 methyl 4-(6,8-dimethyl-1,4-dioxaspiro[4,5]dec-7-en-7-yl)butyrate
  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：

  (-)-(4aR)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione 在 sodium hydroxide 作用下， 以82%的产率得到4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butyric acid
  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

• Intramolecular photoaddition of ketenes to conjugated cycloalkenones
  作者：Dan Becker、Dov Birnbaum

  DOI：10.1021/jo01292a004

  日期：1980.2
• BECKER D.; BIRNBAUM D., J. ORG. CHEM., 1980, 45, NO 4, 570-578
  作者：BECKER D.、 BIRNBAUM D.

  DOI：——

  日期：——
• 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.