1-chloro-1-(4-methoxyphenyl)-5,9-dimethyl-5,9-undecadiene | 205117-86-8

• 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: 1-chloro-1-(4-methoxyphenyl)-5,9-dimethyl-5,9-undecadiene
• 英文别名: 1-[(5E,9E)-1-chloro-5,9-dimethylundeca-5,9-dienyl]-4-methoxybenzene
• CAS: 205117-86-8
• 化学式: C₂₀H₂₉ClO
• 分子量: 320.903
• InChiKey: MCVJCCFOBHUDQB-ZGZOQSPGSA-N

物化性质

• 沸点：
  427.882±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.982±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  10-bromo-3,7-dimethyl-2,6-decadiene 在 氯化亚砜 、 lithium 、 碘甲烷 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， -15.0 ℃ 、74.66 kPa 条件下， 反应 2.0h， 生成 1-chloro-1-(4-methoxyphenyl)-5,9-dimethyl-5,9-undecadiene
  参考文献：
  名称：

  Hammett ρ⁺ Values as Kinetic Evidence for the Concerted Biomimetic Bicyclization Mechanism

  摘要：

  Chlorides 1 (1-aryl-1-chloro-5,9-dimethyl-5,9-undecadienes) with various phenyl substituents were prepared (Y = p-OCH3, p-CH3, H, p-Br, and m-Br), and solvolysis rates were measured in 80% (v/v) aqueous ethanol and in 97% (wt/wt) aqueous 2,2,2-trifluoroethanol. The Hammett rho(+) values obtained are -1.5 and -1.8, respectively, indicating the concerted bicyclization. Comparison with rho(+) values that correspond to solvolysis of the benzylic squalene derivatives 3 (rho(+) = -1.8 and -1.6 in the same solvents) leads to the conclusion of the concerted bicyclization in 3 and may also suggest concerted bicyclization under biomimetic conditions in the natural precursor, 2,3-epoxysqualene, as well.

  DOI：

  10.1021/jo972237s

文献信息

• Hammett ρ⁺ Values as Kinetic Evidence for the Concerted Biomimetic Bicyclization Mechanism
  作者：Ivica Malnar、Krešimir Humski、Olga Kronja

  DOI：10.1021/jo972237s

  日期：1998.5.1

  Chlorides 1 (1-aryl-1-chloro-5,9-dimethyl-5,9-undecadienes) with various phenyl substituents were prepared (Y = p-OCH3, p-CH3, H, p-Br, and m-Br), and solvolysis rates were measured in 80% (v/v) aqueous ethanol and in 97% (wt/wt) aqueous 2,2,2-trifluoroethanol. The Hammett rho(+) values obtained are -1.5 and -1.8, respectively, indicating the concerted bicyclization. Comparison with rho(+) values that correspond to solvolysis of the benzylic squalene derivatives 3 (rho(+) = -1.8 and -1.6 in the same solvents) leads to the conclusion of the concerted bicyclization in 3 and may also suggest concerted bicyclization under biomimetic conditions in the natural precursor, 2,3-epoxysqualene, as well.