(3S,5S)-5-isopropenyl-2-methyl-3-(prop-2'-enyl)-1-trimethylsilyloxy-cyclohex-1-ene | 160837-28-5

• 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: (3S,5S)-5-isopropenyl-2-methyl-3-(prop-2'-enyl)-1-trimethylsilyloxy-cyclohex-1-ene
• 英文别名: trimethyl-[(3S,5S)-2-methyl-5-prop-1-en-2-yl-3-prop-2-enylcyclohexen-1-yl]oxysilane
• CAS: 160837-28-5
• 化学式: C₁₆H₂₈OSi
• 分子量: 264.483
• InChiKey: WOTHLIGGDCGPDB-GJZGRUSLSA-N

物化性质

• 沸点：
  292.261±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.881±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,5S)-5-isopropenyl-2-methyl-3-(prop-2'-enyl)-1-trimethylsilyloxy-cyclohex-1-ene 在 硝基甲烷 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 22.5h， 生成 (4aR,5S,7S)-4,4a,5,6,7,8-hexahydro-7-isopropenyl-4a-methyl-5-(prop-2'-enyl)-naphthalene-2(3H)-one
  参考文献：
  名称：

  S-(+)-carvone as starting material in synthesis (part 4). Conjugate addition of cyanide and Grignard nucleophiles followed by annulation to functionalized decalones.

  摘要：

  Two conjugate addition/annulation methodologies for S-(+)-carvone are reported. The conjugate addition of Grignard reagents, followed by the Lewis acid catalyzed Michael reaction of the intermediate silyl enol ethers with MVK and cyclization of the diketones, gave decalones 2a-d stereoselectively and in good yield. The conjugate addition of cyanide anion followed by base catalyzed Robinson annulation with MVK and dehydration gave decalone 2e stereoselectively in very high yield.

  DOI：

  10.1016/s0040-4020(01)89623-x
• 作为产物：
  描述：

  三甲基氯硅烷 、 右旋香芹酮 、 氯丙烯镁 在 copper(I) bromide dimethylsulfide complex 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.5h， 以7%的产率得到((1S,5S)-1-Allyl-5-isopropenyl-2-methyl-cyclohex-2-enyloxy)-trimethyl-silane
  参考文献：
  名称：

  S-(+)-carvone as starting material in synthesis (part 4). Conjugate addition of cyanide and Grignard nucleophiles followed by annulation to functionalized decalones.

  摘要：

  Two conjugate addition/annulation methodologies for S-(+)-carvone are reported. The conjugate addition of Grignard reagents, followed by the Lewis acid catalyzed Michael reaction of the intermediate silyl enol ethers with MVK and cyclization of the diketones, gave decalones 2a-d stereoselectively and in good yield. The conjugate addition of cyanide anion followed by base catalyzed Robinson annulation with MVK and dehydration gave decalone 2e stereoselectively in very high yield.

  DOI：

  10.1016/s0040-4020(01)89623-x

文献信息

• S-(+)-carvone as starting material in synthesis (part 4). Conjugate addition of cyanide and Grignard nucleophiles followed by annulation to functionalized decalones.
  作者：Anja A. Verstegen-Haaksma、Henk J. Swarts、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/s0040-4020(01)89623-x

  日期：1994.1

  Two conjugate addition/annulation methodologies for S-(+)-carvone are reported. The conjugate addition of Grignard reagents, followed by the Lewis acid catalyzed Michael reaction of the intermediate silyl enol ethers with MVK and cyclization of the diketones, gave decalones 2a-d stereoselectively and in good yield. The conjugate addition of cyanide anion followed by base catalyzed Robinson annulation with MVK and dehydration gave decalone 2e stereoselectively in very high yield.