2-Iodocyclodecan-1-one | 649767-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Iodocyclodecan-1-one
• 英文别名: 2-iodocyclodecan-1-one
• CAS: 649767-27-1
• 化学式: C₁₀H₁₇IO
• 分子量: 280.149
• InChiKey: JOMUWLBBZKPHMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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-Iodocyclodecan-1-one 在 三乙基硼 、 ytterbium(III) triflate 、 烯丙基三甲基硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到环癸酮
  参考文献：
  名称：

  Unexpected nucleophilic behaviour of free-radicals generated from α-iodoketones

  摘要：

  据报道，从α-碘代酮生成的自由基具有意料之外的亲核反应活性；开发了两种不同的方法，一种使用锡，另一种则采用更环保的乙基砜基偶联试剂5c。

  DOI：

  10.1039/b901943j
• 作为产物：
  描述：

  1-trimethylsiloxycyclodecene 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到2-Iodocyclodecan-1-one
  参考文献：
  名称：

  Unexpected nucleophilic behaviour of free-radicals generated from α-iodoketones

  摘要：

  据报道，从α-碘代酮生成的自由基具有意料之外的亲核反应活性；开发了两种不同的方法，一种使用锡，另一种则采用更环保的乙基砜基偶联试剂5c。

  DOI：

  10.1039/b901943j

文献信息

• 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.
• Efficient access to functionalised medium-ring systems by radical fragmentation/radical addition to α-iodoketones
  作者：Corinne De Dobbeleer、Ali Ates、Jean-Christophe Vanherk、István E. Markó

  DOI：10.1016/j.tetlet.2005.03.200

  日期：2005.5

  Functionalised medium-ring systems of various sizes can be efficiently prepared by a novel approach that embodies a radical-induced fragmentation of bicyclic P-hydroxy ketones, followed by a second radical-coupling reaction. The unexpected reactivity of ot-keto radicals is also discussed. (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.
• Unexpected nucleophilic behaviour of free-radicals generated from α-iodoketones
  作者：Corinne De Dobbeleer、Jiří Pospíšil、Freija De Vleeschouwer、Frank De Proft、István E. Markó

  DOI：10.1039/b901943j

  日期：——

  The unexpected nucleophilic reactivity of free-radicals generated from α-iodoketones is reported; two different procedures, either employing tin or the more environmentally acceptable ethylsulfone-based coupling reagent 5c have been developed.

  据报道，从α-碘代酮生成的自由基具有意料之外的亲核反应活性；开发了两种不同的方法，一种使用锡，另一种则采用更环保的乙基砜基偶联试剂5c。