2,7-diiodocycloheptanone | 259173-86-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 2,7-diiodocycloheptanone
• 英文别名: 2,7-Diiodocycloheptan-1-one
• CAS: 259173-86-9
• 化学式: C₇H₁₀I₂O
• 分子量: 363.965
• InChiKey: SAMZDOXCCYLTJW-UHFFFAOYSA-N

物化性质

• 沸点：
  330.1±42.0 °C(Predicted)
• 密度：
  2.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  2,7-diiodocycloheptanone 在 三乙胺 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以82%的产率得到2,7-dihydroxy-cycloheptanone
  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：

  环庚酮 在 cerium (IV) sulfate 、 碘 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以9%的产率得到2,7-diiodocycloheptanone
  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

• Oxidative Synthesis of α,β-Unsaturated Ketone from α-Iodo Ketone Using Peracid
  作者：C. Akira Horiuchi、Shun-Jun Ji、Masatoshi Matsushita、Wen Chai

  DOI：10.1055/s-2003-44371

  日期：——

  Oxidation of α-iodo ketone in CH 2 Cl 2 using m-chloroperbenzoic acid yields α,β-unsaturated ketone by β-H elimination in good yield. This reaction affords a new and convenient synthetic method for α,β-unsaturated ketone from u-iodo ketone.

  使用间氯过苯甲酸在 CH 2 Cl 2 中氧化 α-碘酮，通过 β-H 消除以良好的收率生成 α,β-不饱和酮。该反应为由u-碘酮合成α,β-不饱和酮提供了一种新的、简便的方法。
• 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。
• 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。
• 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.