Z-3-Ethylpent-3-en-2-ol | 83917-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Z-3-Ethylpent-3-en-2-ol
• 英文别名: (Z)-3-ethylpent-3-en-2-ol
• CAS: 83917-05-9
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: PVCQESFACCIIOU-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-乙基-2-戊烯 在 selenium(IV) oxide 、 pinane hydroperoxide 、 溶剂黄146 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 生成 (3Z)-3-乙基-3-戊烯-2-酮 、 Z-3-Ethylpent-3-en-2-ol
  参考文献：
  名称：

  Metal-Catalyzed Oxidations with Pinane Hydroperoxide:  A Mechanistic Probe To Distinguish between Oxometal and Peroxometal Pathways

  摘要：

  The relative reactivities of tert-butyl hydroperoxide (TBHP) and pinane hydroperoxide (PHP) in metal (Cr, Mo, Ru, Se, V, and Zr)-catalyzed oxidations were compared. When these oxidations involve rate-limiting oxygen transfer from a peroxometal species to the substrate huge differences between TBHP and PHP were observed, e.g., molybdenum-catalyzed epoxidation of cyclohexene with TBHP gave a 98% yield while PHP gave 0%. When the reaction involves reaction of an oxometal species with the substrate as the rate-limiting step, little or no difference is observed, e.g., the selenium-catalyzed allylic oxidation of beta-pinene gave a 96% and 99% yield with TBHP and PHP, respectively. Small but significant differences are observed when reoxidation of the catalyst by the hydroperoxide to the active oxometal species is the rate-limiting step; e.g., the chromium-catalyzed oxidation of carveol gave carvone in 89% and 24% yield with TBHP and PHP, respectively. Hence, the effect of RO2H structure on rate is dependent on the rate-limiting step.

  DOI：

  10.1021/jo971270b