1-iodo-2-nonanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-iodo-2-nonanone
• 英文别名: 1-Iodononan-2-one
• 化学式: C₉H₁₇IO
• 分子量: 268.138
• InChiKey: ICCCKHVZTHDTRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  7
• 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

• 作为产物：
  描述：

  2,6-dimethyl-1-(non-1-en-2-yloxy)pyridin-1-ium bis((trifluoromethyl)sulfonyl)amide 在 bis(trifluoromethane)sulfonimide lithium 、 sodium iodide 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 乙腈 为溶剂， 以77%的产率得到1-iodo-2-nonanone
  参考文献：
  名称：

  N-杂环卡宾的弱静电相互作用促进可见光触发的碘化作用。

  摘要：

  N-杂环卡宾（NHC）是众所周知的配体和有机催化剂，但人们尚未认识到它们通过静电相互作用（而不是电子捐赠）作为稳定剂的催化作用。通过利用静电相互作用，我们在本文中描述了可见光触发的N-烯氧基吡啶鎓盐和NaI自由基和自由基的交叉偶联，给出了多种α-碘酮。计算研究表征了NHC的稳定作用。

  DOI：

  10.1021/acs.orglett.0c02523

文献信息

• Oxidative iodination of carbonyl compounds using ammonium iodide and oxone®
  作者：Mahender Reddy Marri、Arun Kumar Macharla、Swamy Peraka、Narender Nama

  DOI：10.1016/j.tetlet.2011.09.106

  日期：2011.12

  A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone® as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones

  通过使用NH 4 I作为碘的来源和Oxone®作为氧化剂，已经报道了一种简单，有效，温和和区域选择性的羰基化合物氧碘化方法。各种羰基化合物（如芳烷基酮，脂族酮（无环和环状）和β-酮酯）以中等至优异的收率发展为各自的α-单碘化产物。不对称脂族酮反应平稳，生成1-碘和3-碘酮的混合物，主要形成1-碘产物。
• 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.
• Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system
  作者：Rok Prebil、Stojan Stavber

  DOI：10.1016/j.tetlet.2014.08.055

  日期：2014.10

  The novel reaction system comprising air/NH4NO3(cat.)/I-2/H2SO4(cat.) is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative a-iodination of aryl, heteroaryl, alkyl, and cycloallcyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved. (C) 2014 Elsevier Ltd. All rights reserved.
• Visible-Light-Triggered Iodinations Facilitated by Weak Electrostatic Interaction of N-Heterocyclic Carbenes
  作者：He Sheng、Qiang Liu、Xiao-Di Su、Yu Lu、Zhi-Xiang Wang、Xiang-Yu Chen

  DOI：10.1021/acs.orglett.0c02523

  日期：2020.9.18

  N-heterocyclic carbenes (NHCs) are well-known as ligands and organocatalysts, but there is no recognition for their catalytic role as a stabilizer through electrostatic interaction rather than electron donation. By utilizing the electrostatic interaction, we herein describe the success of a visible-light-triggered radical–radical cross-coupling of N-alkenoxypyridinium salts and NaI, giving a variety

  N-杂环卡宾（NHC）是众所周知的配体和有机催化剂，但人们尚未认识到它们通过静电相互作用（而不是电子捐赠）作为稳定剂的催化作用。通过利用静电相互作用，我们在本文中描述了可见光触发的N-烯氧基吡啶鎓盐和NaI自由基和自由基的交叉偶联，给出了多种α-碘酮。计算研究表征了NHC的稳定作用。