(-)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal
• 英文别名: 2-[2,2-dimethylcyclopent-3-enyl]-2-hydroxypropanal；(-)-2-(2,2-Dimethyl-cyclo-pent-3-enyl)-2-hydroxypropanal；2-(2,2-dimethylcyclopent-3-en-1-yl)-2-hydroxypropanal
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: QBPSJHLRQMSTJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal 、 2-氨基-4,6-二(2-甲基-2-丙基)苯酚 以 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到2,4-di-tert-butyl-6-{2-[2,2-dimethyl-cyclopent-3-enyl]-2-hydroxypropylideneamino}phenol
  参考文献：
  名称：

  Chiral schiff bases synthesized from terpenes of pinane series in asymmetric metall complex oxidation of sulfides

  摘要：

  The absolute configuration of alpha-hydroxyaldehyde obtained from verbenol epoxide in the presence of clay was determined. Two new Schiff bases were synthesized from the aldehyde obtained. The compounds can be used as ligands in the asymmetric vanadium-catalyzed oxidation of sulfides to sulfoxides. The structure of initial sulfides significantly affects the value of the enantiomeric excess in the obtained sulfoxides: the highest enantiomeric excess is observed in the oxidation of thioanisole.

  DOI：

  10.1134/s1070428012020108
• 作为产物：
  描述：

  (-)-α-蒎烯 在 lithium aluminium tetrahydride 、 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 57.75h， 生成 (1R,2R,6S)-3-methyl-6-(1-methylethenyl)cyclohex-3-ene-1,2-diol 、 (S)-2-hydroxy-1-(2,2,3-trimethylcyclopent-3-enyl)ethanone 、 4-异丙基甲苯 、 (-)-2-(2,2-dimethylcyclopent-3-enyl)-2-hydroxypropanal
  参考文献：
  名称：

  Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease

  摘要：

  (1R,2R,6S)-3-甲基-6-(丙-1-烯-2-基)环己-3-烯-1,2-二醇 1 在 MPTP 和氟哌啶醇动物模型中均表现出强效的抗帕金森症活性。使用化合物 1 能使运动和探索活动几乎完全恢复，其效果与对照药物（左旋多巴）相当。化合物 1 的八个立体异构体均已被合成，且其绝对构型对抗帕金森症活性的影响也已得到验证。

  DOI：

  10.1021/jm2001579

文献信息

• Highly Potent Activity of (1<i>R</i>,2<i>R</i>,6<i>S</i>)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease
  作者：Oleg V. Ardashov、Alla V. Pavlova、Irina V. Il’ina、Ekaterina A. Morozova、Dina V. Korchagina、Elena V. Karpova、Konstantin P. Volcho、Tat’yana G. Tolstikova、Nariman F. Salakhutdinov

  DOI：10.1021/jm2001579

  日期：2011.6.9

  (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 1 possesses potent antiparkinsonian activity in both MPTP and haloperidol animal models. The use of compound 1 resulted in nearly full recovery of the locomotor and exploratory activities and was as effective as the comparator agent (levodopa). All eight stereoisomers of compound 1 have been synthesized and the influence of the absolute configuration on the antiparkinsonian activity of compound 1 was shown.

  (1R,2R,6S)-3-甲基-6-(丙-1-烯-2-基)环己-3-烯-1,2-二醇 1 在 MPTP 和氟哌啶醇动物模型中均表现出强效的抗帕金森症活性。使用化合物 1 能使运动和探索活动几乎完全恢复，其效果与对照药物（左旋多巴）相当。化合物 1 的八个立体异构体均已被合成，且其绝对构型对抗帕金森症活性的影响也已得到验证。
• Chiral schiff bases synthesized from terpenes of pinane series in asymmetric metall complex oxidation of sulfides
  作者：I. V. Il’ina、E. A. Koneva、D. V. Korchagina、G. E. Sal’nikov、A. M. Genaev、K. P. Volcho、N. F. Salakhutdinov

  DOI：10.1134/s1070428012020108

  日期：2012.2

  The absolute configuration of alpha-hydroxyaldehyde obtained from verbenol epoxide in the presence of clay was determined. Two new Schiff bases were synthesized from the aldehyde obtained. The compounds can be used as ligands in the asymmetric vanadium-catalyzed oxidation of sulfides to sulfoxides. The structure of initial sulfides significantly affects the value of the enantiomeric excess in the obtained sulfoxides: the highest enantiomeric excess is observed in the oxidation of thioanisole.