2-hydroxy-3,6-dimethyl-2-cyclohexenone | 2748-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3,6-dimethyl-2-cyclohexenone
• 英文别名: 3,6-dimethyl-1,2-cyclohexanedione；2-Hydroxy-3,6-dimethyl-2-cyclohexen-1-one；2-hydroxy-3,6-dimethylcyclohex-2-en-1-one
• CAS: 2748-08-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: VPPPLRGAPXVWJO-UHFFFAOYSA-N

物化性质

• 熔点：
  61.5-62.5 °C
• 沸点：
  263.0±40.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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-hydroxy-3,6-dimethyl-2-cyclohexenone 在 air 2,4-二氯苯氧乙酸 、 Marchantia polymorpha cells 、 Murashige Skoog medium 作用下， 以 乙醚 为溶剂， 反应 192.0h， 生成 methyl 2-methyl-5-oxohexanoate
  参考文献：
  名称：

  Oxidative cleavage of the C–C bond of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha

  摘要：

  Biotransformation of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha involves regioselective oxidative cleavage of the C-C bond to give the corresponding oxocarboxylic acids shortened by one carbon unit. In the case of cyclohexane-1,2-dione, adipic acid was obtained. (C) 2002 Elsevier Science Ltd. All rights, reserved.

  DOI：

  10.1016/s0031-9422(02)00373-4
• 作为产物：
  描述：

  2-羟基-2-环己烯-1-酮 在 溶剂黄146 、 锌 作用下， 生成 2-hydroxy-3,6-dimethyl-2-cyclohexenone
  参考文献：
  名称：

  脂环族α-二酮的曼尼希反应。2-Hydroxy-3-methyl-2-cyclohexen-1-one的新合成

  摘要：

  描述了 2-羟基-3-甲基-2-环己烯-1-one (1) 的新合成。环己烷-1,2-二酮 (2) 或 2-morpholino-2-cyclohexen-1-one (3) 与吗啉和福尔马林的曼尼希反应得到曼尼希碱 (4)，然后将其氢解得到 1。然而，1 的曼尼希反应仅产生双曼尼希碱 (22)，然后类似地将其氢化以提供 3,6-二甲基-2-羟基-2-环己烯-1-酮 (7) 以及 3,6-二甲基-2-羟基-6-吗啉甲基-2-环己烯-1-one (26); 在这些条件下无法获得 2-hydroxy-3,6,6-trimethyl-2-cyclohexen-1-one。还描述了其他脂环族α-二酮的曼尼希反应及其曼尼希碱的氢解。

  DOI：

  10.1246/bcsj.48.1892

文献信息

• A New Synthesis of 3-Alkyl-1,2-cyclohexanediones from 2- Alkylcyclohexanones Using Iodine/Copper(II) Acetate
  作者：C. Akira Horiuchi、Hiroshi Kiyomiya、Masaaki Takahashi、Yasuto Suzuki

  DOI：10.1055/s-1989-27397

  日期：——

  The reactions of 2-alkyl-, 2,5-dimethyl-, and 3,3,5-trimethylcyclohexanone with iodine/copper(II) acetate in boiling aqueous acetic acid gave the respective 3-alkyl-, 3,6-dimethyl-, and 3,5,5-trimethyl-1,2-cyclohexanediones in 40-70% yields. This new synthetic method is more convenient than the methods used heretofore.

  2-烷基、2,5-二甲基和3,3,5-三甲基环己酮与碘/醋酸铜(II)在沸腾的水合醋酸中反应，得到了相应的3-烷基、3,6-二甲基和3,5,5-三甲基-1,2-环己二酮，产率为40-70%。这种新的合成方法比之前使用的方法更加方便。
• A New Synthesis of 3-Hydroxy-2,5-dialkyl-1,4-benzoquinones Using Iodine-Copper(II) Acetate
  作者：C. Akira Horiuchi、Yasuto Suzuki、Masaaki Takahashi、J. Yasuo Satoh

  DOI：10.1246/cl.1987.393

  日期：1987.2.5

  Reactions of diosphenol and 3,6-dimethyl-1,2-cyclohexanedione with iodine-copper(II) acetate in acetic acid-water (5:1) at 80 °C gave the respective 3-hydroxy-2,5-dialkyl-1,4-benzoquinone in 25–80% yields. 2-t-Butyl-5-methylcyclohexanone similarly gave the corresponding 3-hydroxy-1,4-benzoquinone in 66% yield.

  在80°C下，二苯酚和3,6-二甲基-1,2-环己烷二酮与碘-铜(II)醋酸盐在醋酸-水（5:1）中反应，分别得到了相应的3-羟基-2,5-二烷基-1,4-苯醌，产率为25-80%。2-t-丁基-5-甲基环己酮同样得到了相应的3-羟基-1,4-苯醌，产率为66%。
• A New Synthesis of 3-Hydroxy-2,5-dialkyl-1,4-benzoquinone from 3-Halo-3,6-dialkyl-1,2-cyclohexanedione Using Iodine–Copper(II) Acetate
  作者：C. Akira Horiuchi、Yasuto Suzuki

  DOI：10.1246/bcsj.62.2919

  日期：1989.9

  The reaction of 3-iodo-3,6-dialkyl-1,2-cyclohexanedione (2) with iodine–copper(II) acetate in acetic acid–water (5:1) at 80 °C gave the respective 3-hydroxy-2,5-dialkyl-1,4-benzoquinone in 38–80% yields. On the other hand, the reaction of 2 with copper(II) acetate in acetic acid–water (10:1) under refluxing afforded the respective 3,3′-dihydroxy 2,2′,5,5′-tetraalkyl-4,4′-diphenoquinone (5) in 41–85%

  3-碘-3,6-二烷基-1,2-环己二酮 (2) 与碘-乙酸铜 (II) 在乙酸-水 (5:1) 中在 80 °C 下反应得到各自的 3-羟基- 2,5-二烷基-1,4-苯醌的产率为 38-80%。另一方面，2与乙酸铜（II）在乙酸-水（10:1）中回流反应得到各自的3,3'-二羟基2,2',5,5'-四烷基-4， 4'-二苯醌 (5) 的产率为 41–85%。在3-溴-3,6-二烷基衍生物(3)与乙酸铜(II)的情况下，得到二苯醌衍生物和3-羟基-2,5-二烷基-1,4-苯醌。
• REGIOSELECTIVE MONOALKYLATION OF 3-METHYL-1,2-CYCLOHEXANEDIONE
  作者：Masanori Utaka、Makoto Hojo、Akira Takeda

  DOI：10.1246/cl.1984.445

  日期：1984.3.5

  Monoalkylation of 3-methyl-1,2-cyclohexanedione was achieved regioselectively to give 6-alkyl-3-methyl-1,2-cyclohexanedione as a major product without the formation of O-alkylated or polyalkylated products.

  3-甲基-1,2-环己二酮的单烷基化区域选择性地得到6-烷基-3-甲基-1,2-环己二酮作为主要产物，而没有形成O-烷基化或多烷基化产物。
• Photo-irradiation of α-halo carbonyl compounds: a novel synthesis of α-hydroxy- and α,α′-dihydroxyketones
  作者：Wen Chai、Akihiro Takeda、Makoto Hara、Shun-Jun Ji、C. Akira Horiuchi

  DOI：10.1016/j.tet.2005.01.010

  日期：2005.2

  The reaction of g.-halo ketones (alpha-iodocycloalkanones, alpha-bromocycloalkanones, alpha-iodo-beta-alkoxy esters, and alpha-iodoacyclic-ketones) with irradiation under a high-pressure mercury lamp gave the corresponding alpha-hydroxyketones in good yields. For alpha-bromoketones, it was found that alpha-hydroxylation does not occur. However, alpha-bromoketones were convened into a-hydroxyketones in the presence of KI. In the case of alpha,alpha(1)-diiodo ketones, alpha,alpha(1)-dihydroxyketones, which up to now have scarcely been reported, were obtained. This reaction affords a new, clean and convenient synthetic method for alpha-hydroxy- and alpha,alpha(1)-dihydroxyketones. (C) 2005 Elsevier Ltd. All rights reserved.