meso-4,6-diiodo-5-nonanone | 259173-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: meso-4,6-diiodo-5-nonanone
• 英文别名: 4,6-diiodononan-5-one
• CAS: 259173-85-8
• 化学式: C₉H₁₆I₂O
• 分子量: 394.034
• InChiKey: ZDTYFAKKHDKIEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  meso-4,6-diiodo-5-nonanone 在 三乙胺 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以65%的产率得到4,6-dihydroxy-5-nonanone
  参考文献：
  名称：

  A novel synthesis of α-hydroxy- and α,α′-dihydroxyketone from α-iodo and α,α′-diiodo ketone using photoirradiation

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2003.10.082
• 作为产物：
  描述：

  5-壬酮 在 ammonium cerium(IV) nitrate 、 碘 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 15.0h， 生成 meso-4,6-diiodo-5-nonanone 、 dl-4,6-diiodo-5-nonanone
  参考文献：
  名称：

  A Newα,α′-Diiodination of Ketones Using Iodine-Cerium(IV) Ammonium Nitrate

  摘要：

  使用碘-铈(IV)硝酸铵在乙酸或丙酮中直接碘化一些酮，可以高收率地得到相应的α,α′-二碘酮。对于环十二烷酮(4)、3-戊酮(5)和5-壬酮(6)，优先得到顺式(内消旋)化合物[2,12-二碘环十二烷酮(12)、2,4-二碘-3-戊酮(13)和4,6-二碘-5-壬酮(14)]。

  DOI：

  10.1246/bcsj.67.271

文献信息

• m-Iodosylbenzoic Acid as a Convenient Recyclable Hypervalent Iodine Oxidant for the Synthesis of α-Iodo Ketones by Oxidative Iodination of Ketones
  作者：Mehman Yusubov、Viktor Zhdankin、Rosa Yusubova、Tatyana Funk、Ki-Whan Chi、Andreas Kirschning

  DOI：10.1055/s-0030-1258223

  日期：2010.11

  A convenient procedure for the preparation of α-iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and β-dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective α-iodo-substituted carbonyl compounds in excellent yields. The final products of

  使用用于通过酮的氧化碘化制备α碘酮的方便方法碘和中号作为可回收高价碘氧化剂报道-iodosylbenzoic酸。该试剂体系可以在温和的条件下碘化各种酮和β-二羰基化合物，从而以优异的产率提供各自的α-碘取代的羰基化合物。碘化的最终产物可方便地从由副产物简单处理分离与阴离子交换树脂的Amberlite IRA 900 HCO 3 -和蒸发溶剂后以良好的纯度分离出来。高价碘氧化剂的还原形式m通过用盐酸水溶液处理，然后用乙酸乙酯萃取，可以以91-95％的收率从Amberlite树脂中回收-碘苯甲酸。 卤化-碘-酮-亚碘酰苯-米-iodosylbenzoic酸-高价碘
• Synthesis of α,β-unsaturated ketone from α-iodo ketone using photoirradiation
  作者：Shun-Jun Ji、Eiji Takahashi、T.Tomoyoshi Takahashi、C.Akira Horiuchi

  DOI：10.1016/s0040-4039(99)02010-9

  日期：1999.12

  Irradiation of α-iodo ketone in hexane under a nitrogen atmosphere with a high-pressure mercury lamp (λ>300nm) at room temperature afforded the corresponding α,β-unsaturated ketones in good yield. This reaction affords a new, clean and convenient synthetic method for the α,β-unsaturated ketone.

  在室温下在氮气气氛下用高压汞灯（λ> 300nm）照射α-碘酮在己烷中的辐射，以良好的收率得到相应的α，β-不饱和酮。该反应为α，β-不饱和酮提供了一种新的，清洁的和方便的合成方法。
• 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.