R-(-)-carveol

• 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: R-(-)-carveol
• 英文别名: (1R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-ol
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: BAVONGHXFVOKBV-QVDQXJPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  R-(-)-carveol 在 叔丁基过氧化氢 、 Λ-(+)-tris(acetylacetonato)chromium(III) 作用下， 以 氯苯 为溶剂， 反应 5.0h， 生成 香芹酮
  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
• 作为产物：
  描述：

  R-(+)-1,2-limonene epoxide 、 zinc 2-ethylhexanoate 、 2-氨基苯酚 生成 R-(-)-carveol
  参考文献：
  名称：

  Catalyst system and process for rearrangement of epoxides to allylic alcohols

  摘要：

  一种催化剂系统可用于实现(a)通过重排相应环氧化物制备烯丙基醇，当烯丙基醇是所需的产物时；(b)随后的反应，例如选择性氧化，将在步骤(a)中获得的烯丙基醇转化为所需的产物，例如α，β-不饱和羰基化合物；和/或(c)能够在一个锅中进行步骤a)和b)。在一个实施例中，该催化剂系统包括(i)至少包括一个初级催化剂的催化剂包括一个或多个均相或异相的、无机的、有机的或复杂的含金属化合物，以及(ii)至少包括一种苯酚化合物的活化剂/改性剂。

  公开号：

  US20030065230A1

文献信息

• Metal-Catalyzed Oxidations with Pinane Hydroperoxide:  A Mechanistic Probe To Distinguish between Oxometal and Peroxometal Pathways
  作者：H. E. B. Lempers、A. Ripollès i Garcia、R. A. Sheldon

  DOI：10.1021/jo971270b

  日期：1998.3.1

  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.
• Catalyst system and process for rearrangement of epoxides to allylic alcohols
  申请人：——

  公开号：US20030065230A1

  公开（公告）日：2003-04-03

  A catalyst system that can be used to achieve (a) preparation of allylic alcohols by rearrangement of the corresponding epoxide, when the allylic alcohol is a desired product; (b) subsequent reaction, e.g., selective oxidation, of the allylic alcohols obtained in step (a) to afford a desired product, e.g., alpha, beta-unsaturated carbonyl compounds; and/or (c) the ability to perform steps a) and b) in a one-pot process. In one embodiment, the catalyst system includes (i) at least one primary catalyst includes one or more homogeneous or heterogeneous, inorganic, organic or complex metal-containing compound, and (ii) at least one activator/modifier comprising at least one phenolic compound.

  一种催化剂系统可用于实现(a)通过重排相应环氧化物制备烯丙基醇，当烯丙基醇是所需的产物时；(b)随后的反应，例如选择性氧化，将在步骤(a)中获得的烯丙基醇转化为所需的产物，例如α，β-不饱和羰基化合物；和/或(c)能够在一个锅中进行步骤a)和b)。在一个实施例中，该催化剂系统包括(i)至少包括一个初级催化剂的催化剂包括一个或多个均相或异相的、无机的、有机的或复杂的含金属化合物，以及(ii)至少包括一种苯酚化合物的活化剂/改性剂。