6-isopropenyl-3-methyl-1-(1-naphthalen-1-yl-vinyl)-cyclohex-2-enol | 848122-23-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 6-isopropenyl-3-methyl-1-(1-naphthalen-1-yl-vinyl)-cyclohex-2-enol
• 英文别名: (1S,6S)-3-methyl-1-(1-naphthalen-1-ylethenyl)-6-prop-1-en-2-ylcyclohex-2-en-1-ol
• CAS: 848122-23-6
• 化学式: C₂₂H₂₄O
• 分子量: 304.432
• InChiKey: BBGLVCXBZHDDFP-FCHUYYIVSA-N

物化性质

• 沸点：
  445.3±45.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-isopropenyl-3-methyl-1-(1-naphthalen-1-yl-vinyl)-cyclohex-2-enol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 7-methyl-4-methylene-2,3,4,4a,5,6-hexahydro-1H-[1,1']-binaphthalenyl-8a-ol 、 7-methyl-4-methylene-2,3,4,4a,5,6-hexahydro-1H-[1,1']-binaphthalenyl-8a-ol
  参考文献：
  名称：

  Conservation of the Planar Chiral Information in the Tandem Oxy-Cope/Ene Reaction

  摘要：

  We report the stereoselective synthesis of a Decalin unit using a tandem oxy-Cope/ene reaction. [3,3]-Shift of 1,2-divinyleyclohexenol 18 generates (1E, 3Z, 7E) cyclodecatrien-2-ol 23 which tautomerizes to ketone 21 (Figure 3). The chiral information embedded in 23 is transferred into the newly formed stereogenic carbon C6 in 21. The efficiency of the chirality transfer is a reflection of the difference in the rates of ring inversion versus tautomerization of 23. Ketone 21 undergoes a carbonyl-ene reaction to give Decalin 20. Assuming a rapid equilibrium between macrocyclic diastereomers, the diastereomeric ratio of the transannular ene reaction is governed by the Curtin-Hammett principle. Analysis of the conservation of the planar chiral information in the tandem oxy-Cope/ene reaction is presented.

  DOI：

  10.1021/jo047916z
• 作为产物：
  描述：

  在 叔丁基锂 、 溶剂黄146 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 6-isopropenyl-3-methyl-1-(1-naphthalen-1-yl-vinyl)-cyclohex-2-enol
  参考文献：
  名称：

  Conservation of the Planar Chiral Information in the Tandem Oxy-Cope/Ene Reaction

  摘要：

  We report the stereoselective synthesis of a Decalin unit using a tandem oxy-Cope/ene reaction. [3,3]-Shift of 1,2-divinyleyclohexenol 18 generates (1E, 3Z, 7E) cyclodecatrien-2-ol 23 which tautomerizes to ketone 21 (Figure 3). The chiral information embedded in 23 is transferred into the newly formed stereogenic carbon C6 in 21. The efficiency of the chirality transfer is a reflection of the difference in the rates of ring inversion versus tautomerization of 23. Ketone 21 undergoes a carbonyl-ene reaction to give Decalin 20. Assuming a rapid equilibrium between macrocyclic diastereomers, the diastereomeric ratio of the transannular ene reaction is governed by the Curtin-Hammett principle. Analysis of the conservation of the planar chiral information in the tandem oxy-Cope/ene reaction is presented.

  DOI：

  10.1021/jo047916z