3-碘辛烷-2-酮 | 73746-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-碘辛烷-2-酮
• 英文名称: 3-iodo-2-octanone
• 英文别名: iodo-3 octanone-2；3-iodo-octane-2-one；3-iodooctan-2-one
• CAS: 73746-49-3
• 化学式: C₈H₁₅IO
• 分子量: 254.111
• InChiKey: TYVWXCCVZJWMTK-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 0.1 Torr)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  3-碘辛烷-2-酮 、 乙二醇 以 苯 为溶剂， 反应 12.0h， 以50%的产率得到(iodo-1 hexyl)-2 methyl-2 dioxolanne-1,3
  参考文献：
  名称：

  Daubie, Christophe; Bacquet-Einhorn, Cathy; Lelandais, Daniel, Canadian Journal of Chemistry, 1984, vol. 62, p. 1548 - 1551

  摘要：

  DOI：
• 作为产物：
  描述：

  仲辛酮 在 碘 、 mercury dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以74%的产率得到3-碘辛烷-2-酮
  参考文献：
  名称：

  Mercury(II) Chloride-Iodine: A Useful Reagent for the Direct and Regiospecific Synthesis of α-Iodocarbonyl Compounds

  摘要：

  DOI：

  10.1055/s-1986-31748

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
• Chemistry of α-nitroepoxides : Synthesis of useful intermediates via nucleophilic ring opening of α-nitroepoxides
  作者：Yashwant D. Vankar、Kavita Shah、Anita Bawa、Surendra P. Singh

  DOI：10.1016/s0040-4020(01)81002-4

  日期：1991.10

  Various α-nitroepoxides are converted into corresponding 1,2-diketones via two different ways of ring opening viz. with Pd(O) and with DMSO/BF3·Et2O(or ClSiMe3). In addition to this, a variety of nucleophiles are reacted with α-nitrocyclopentene oxide 6 and α-nitro-cyclohexene oxide 7 to form the corresponding α-substituted ketones which are useful intermediates in organic synthesis. Two of the products

  各种α-硝基环氧化物通过两种不同的开环方式转化为相应的1,2-二酮。用Pd（O）和DMSO / BF 3 ·Et 2 O（或ClSiMe 3）。除此之外，各种亲核试剂与α-硝基环戊烯氧化物6和α-硝基环己烯氧化物7反应以形成相应的α-取代的酮，其在有机合成中是有用的中间体。这样获得的两种产品即。还通过面包酵母的还原然后内酯化将32和33分别进一步转化为旋光的内酯38和39。
• One-pot synthesis of α-iodoketones from alcohols using ammonium iodide and Oxone® in water
  作者：Marri Mahender Reddy、Peraka Swamy、Mameda Naresh、Kodumuri Srujana、Chevella Durgaiah、Tumula Venkateshwar Rao、Nama Narender

  DOI：10.1039/c4ra16130k

  日期：——

  A novel protocol for the synthesis of α-iodoketones from alcohols has been developed. Using water as the reaction medium, ammonium iodide and Oxone® was proven to be an efficient reagent system for this reaction and afforded the corresponding α-iodoketones in moderate to good yields. The generality of this reaction was demonstrated with various secondary alcohols such as benzylic alcohols and aliphatic

  已经开发了一种从醇类合成α-碘酮的新方案。使用水作为反应介质，碘化铵和Oxone®被证明是该反应的有效试剂系统，并以中等至良好的产率提供了相应的α-碘酮。用各种仲醇如苄醇和脂族醇（无环和环状）证明了该反应的一般性。
• Metal catalyst-free direct α-iodination of ketones with molecular iodine
  作者：Maddali L.N. Rao、Deepak N. Jadhav

  DOI：10.1016/j.tetlet.2006.07.057

  日期：2006.9

  Ketones are directly converted to the corresponding alpha-iodoketones in good yields with molecular iodine under metal catalyst-free conditions. A significant difference in the reactivities was observed for aliphatic and aromatic ketones; whereas aliphatic ketones reacted smoothly at room temperature giving a mixture of 1-iodo, 3-iodo and 1,3-diiodoketones with predominant formation of the 3-iodo product, the a-iodination of aromatic ketones proceeded conveniently under heating to give good yields of alpha-iodo products. (c) 2006 Elsevier Ltd. All rights reserved.
• Vankar, Yashwant D.; Saksena, Rajendra K.; Bawa, Anita, Chemistry Letters, 1989, p. 1241 - 1244
  作者：Vankar, Yashwant D.、Saksena, Rajendra K.、Bawa, Anita

  DOI：——

  日期：——