(4aS,5R,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnaphthalen-1-one | 213247-76-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4aS,5R,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnaphthalen-1-one
• 英文别名: methyl 2-[(1S,4aS,8aS)-1,4a,6-trimethyl-5-oxo-8,8a-dihydro-4H-naphthalen-1-yl]acetate
• CAS: 213247-76-8
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: GCSDTNIJSGUQSR-MAZHCROVSA-N

物化性质

• 沸点：
  347.5±42.0 °C(predicted)
• 密度：
  1.048±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aS,5R,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnaphthalen-1-one 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 22.0h， 以97%的产率得到(4aS,5R,8aS)-1,4,4a,5,8,8a-hexahydro-1-oxo-2,5,8a-trimethylnaphthalen-5-acetic acid
  参考文献：
  名称：

  Palladium-Mediated Ring Closure Reactions. Facile Syntheses of Enantiopure Bicyclic and Tricyclic Alkenones

  摘要：

  (R)-Carvone was used as a chiral building block. Regio- and stereoselective alkylations at C6 and C2 of (R)-carvone and (R)-5-isopropyl-2-methyl-2-cyclohexenone [derived from the hydrogenation of (R)-carvone] followed by palladium-mediated ring closures afforded various enantiopure bicyclic and tricyclic alkenones. Hence, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone (3) gave (4aS,5S,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnapthalen-1-one (7) as the major product, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropyl-2-cyclohex (22) produced (1S,5R,6S)-1,5-dimethyl-6-isopropyltricyclo[3.3.1.0(2,8)]-3-nonen-9-one (23), and cyclization of (2R,5S,6S)-2,6-dimethyl-2-(cis-3-iodo-2-propenyl)-5-isopropenyl-3-cyclohexen- 1-one (25) afforded (3aR,6S,7aR)-6,7a-dimethyl-5-isopropenyl-3a,6,7,7a-tetrahydro-1H-inden-7-one (26). A 1,2-rearrangement reaction of bromide 16 gave hexahydro-1H-benzocycloheptene 17. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00658-x
• 作为产物：
  描述：

  2-环己烯-1-酮,2,6-二甲基-5-(1-甲基乙烯基)-,(5R)- 在 六甲基磷酰三胺 、 palladium diacetate 、 三苯基膦 、 silver carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 (4aS,5R,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnaphthalen-1-one
  参考文献：
  名称：

  Palladium-Mediated Ring Closure Reactions. Facile Syntheses of Enantiopure Bicyclic and Tricyclic Alkenones

  摘要：

  (R)-Carvone was used as a chiral building block. Regio- and stereoselective alkylations at C6 and C2 of (R)-carvone and (R)-5-isopropyl-2-methyl-2-cyclohexenone [derived from the hydrogenation of (R)-carvone] followed by palladium-mediated ring closures afforded various enantiopure bicyclic and tricyclic alkenones. Hence, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone (3) gave (4aS,5S,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnapthalen-1-one (7) as the major product, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropyl-2-cyclohex (22) produced (1S,5R,6S)-1,5-dimethyl-6-isopropyltricyclo[3.3.1.0(2,8)]-3-nonen-9-one (23), and cyclization of (2R,5S,6S)-2,6-dimethyl-2-(cis-3-iodo-2-propenyl)-5-isopropenyl-3-cyclohexen- 1-one (25) afforded (3aR,6S,7aR)-6,7a-dimethyl-5-isopropenyl-3a,6,7,7a-tetrahydro-1H-inden-7-one (26). A 1,2-rearrangement reaction of bromide 16 gave hexahydro-1H-benzocycloheptene 17. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00658-x

文献信息

• US5958970A
  申请人：——

  公开号：US5958970A

  公开（公告）日：1999-09-28
• US6384045B1
  申请人：——

  公开号：US6384045B1

  公开（公告）日：2002-05-07
• Palladium-Mediated Ring Closure Reactions. Facile Syntheses of Enantiopure Bicyclic and Tricyclic Alkenones
  作者：Duy H Hua、Kiyosei Takasu、Xiaodong Huang、Gail S Millward、Yi Chen、Jingmei Fan

  DOI：10.1016/s0040-4020(00)00658-x

  日期：2000.9

  (R)-Carvone was used as a chiral building block. Regio- and stereoselective alkylations at C6 and C2 of (R)-carvone and (R)-5-isopropyl-2-methyl-2-cyclohexenone [derived from the hydrogenation of (R)-carvone] followed by palladium-mediated ring closures afforded various enantiopure bicyclic and tricyclic alkenones. Hence, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone (3) gave (4aS,5S,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnapthalen-1-one (7) as the major product, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropyl-2-cyclohex (22) produced (1S,5R,6S)-1,5-dimethyl-6-isopropyltricyclo[3.3.1.0(2,8)]-3-nonen-9-one (23), and cyclization of (2R,5S,6S)-2,6-dimethyl-2-(cis-3-iodo-2-propenyl)-5-isopropenyl-3-cyclohexen- 1-one (25) afforded (3aR,6S,7aR)-6,7a-dimethyl-5-isopropenyl-3a,6,7,7a-tetrahydro-1H-inden-7-one (26). A 1,2-rearrangement reaction of bromide 16 gave hexahydro-1H-benzocycloheptene 17. (C) 2000 Elsevier Science Ltd. All rights reserved.