3-iodo-3,6-dimethyl-1,2-cyclohexanedione | 110364-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-iodo-3,6-dimethyl-1,2-cyclohexanedione
• 英文别名: 2-Hydroxy-6-iodo-3,6-dimethylcyclohex-2-en-1-one
• CAS: 110364-41-5
• 化学式: C₈H₁₁IO₂
• 分子量: 266.079
• InChiKey: BTNJMUMMIUDIIL-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  329.4±42.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 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：

  3-iodo-3,6-dimethyl-1,2-cyclohexanedione 以34%的产率得到
  参考文献：
  名称：

  HORIUCHI C. AKIRA; SUZUKI YASUTO; TAKAHASHI MASAAKI; SATOH J. YASUO, CHEM. LETT.,(1987) N 2, 393-396

  摘要：

  DOI：
• 作为产物：
  描述：

  3,6-dimethyl-1,2-cyclohexanedione 以83%的产率得到
  参考文献：
  名称：

  HORIUCHI C. AKIRA; SUZUKI YASUTO; TAKAHASHI MASAAKI; SATOH J. YASUO, CHEM. LETT.,(1987) N 2, 393-396

  摘要：

  DOI：

文献信息

• 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。
• 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.
• A novel synthesis of α-hydroxy- and α,α′-dihydroxyketone from α-iodo and α,α′-diiodo ketone using photoirradiation
  作者：C.Akira Horiuchi、Akinori Takeda、Wen Chai、Kishoh Ohwada、Shun-Jun Ji、T.Tomoyoshi Takahashi

  DOI：10.1016/j.tetlet.2003.10.082

  日期：2003.12

  A novel reaction of alpha-iodo ketone (alpha-iodocycloalkanone, alpha-iodo-beta-alkoxy ester, and alpha-iodoacyclicketone) with irradiation under a high-pressure mercury lamp gave the corresponding alpha-hydroxyketone in good yields. In the case of alpha,alpha'-diiodo ketone, alpha,alpha'-dihydroxyketone which little has been reported until now was obtained. This reaction affords a new, clean and convenient synthetic method for alpha-hydroxy- and alpha,alpha'-dihydroxyketone. (C) 2003 Elsevier Ltd. All rights reserved.