(5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone | 213247-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone
• 英文别名: (5S,6S)-6-[(Z)-3-iodoprop-2-enyl]-2,6-dimethyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
• CAS: 213247-68-8
• 化学式: C₁₄H₁₉IO
• 分子量: 330.209
• InChiKey: VGPVPXHZSULHGQ-WTOLDRAOSA-N

物化性质

• 沸点：
  355.8±31.0 °C(predicted)
• 密度：
  1.349±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone 在 palladium diacetate 、 氢氧化钾 、 草酰氯 、 N-hydroxy-2-thiopyridinone 、 sodium hydride 、 三苯基膦 、 silver carbonate 、 三甲氧基磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 67.0h， 生成 (4aS,5S,8aS)-1,4,4a,5,8,8a-hexahydro-5-(hydroxymethyl)-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
• 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)- 、 (Z)-1-iodo-3-methanesulfonyloxy-1-propene 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 16.0h， 以73%的产率得到(5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone
  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