2-iodo-1-(2-naphthalenyl)ethanone | 55116-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-iodo-1-(2-naphthalenyl)ethanone
• 英文别名: 2-iodo-1-(naphthalen-2-yl)ethanone；2-Iodo-1-(naphthalen-2-yl)ethan-1-one；2-iodo-1-naphthalen-2-ylethanone
• CAS: 55116-99-9
• 化学式: C₁₂H₉IO
• 分子量: 296.107
• InChiKey: USSYWBMZTAVASW-UHFFFAOYSA-N

物化性质

• 沸点：
  387.0±25.0 °C(Predicted)
• 密度：
  1.702±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-iodo-1-(2-naphthalenyl)ethanone 在 水 、 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate 作用下， 125.0 ℃ 、344.74 kPa 条件下， 反应 0.03h， 以90%的产率得到2-萘乙酮
  参考文献：
  名称：

  Ionic liquid promoted selective debromination of α-bromoketones under microwave irradiation

  摘要：

  The debrontination of alpha-bromoketones with an easily accessible ionic liquid, 1-methyl-3-pentylimidazolium tetrafluoroborate, [pmIm]BF4 under microwave irradiation has been investigated. By controlling the reaction time gem-alpha-dibromoketones are selectively debrominated to either monobromo or debromoketones. The alpha-monobromo- and alpha-monoiodoketones are dehalogenated while the corresponding chloroketones remain inert. The activated vic-bromoacetates are converted to the corresponding (E)-alkenes by the same procedure. These reactions do not require any organic solvent, any metal or any conventional reducing agent. The ionic liquid works here as catalyst as well as reaction medium and is recycled without any appreciable loss of its catalytic efficiency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.035
• 作为产物：
  描述：

  2-萘乙酮 在 碘 、 copper(II) oxide 作用下， 以 乙醇 为溶剂， 生成 2-iodo-1-(2-naphthalenyl)ethanone
  参考文献：
  名称：

  I 2 / CuO催化串联环化策略，可从易于获得的芳族酮/α，β-不饱和酮和硫脲一锅法合成取代的2-氨基噻唑

  摘要：

  开发了一种由易得的甲基酮/不饱和甲基酮和硫脲组成的简洁高效的一锅法，用于在I 2 / CuO介质下合成2-氨基噻唑。该方法可以高度立体选择性地获得4-乙烯基-2-氨基噻唑的电子异构体（5a–f）。所有这些目标分子均通过NMR，HRMS和IR光谱进行了表征。此外，通过X射线晶体学分析进一步确定目标化合物3c和5b。

  DOI：

  10.1016/j.tet.2011.10.074

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。
• A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives
  作者：Qun Cai、Yan-Ping Zhu、Yang Gao、Jing-Jing Sun、An-Xin Wu

  DOI：10.1139/cjc-2012-0534

  日期：2013.6

  A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylide synthesis, and 1,3-dipolar cycloaddition. The protocols were found to be highly efficient in terms of high yields, operational simplicity, mild reaction conditions, and easy workup. This method has provided an important supplement for the synthesis of indolizine derivatives via a novel tandem synthesis.

  已提出一种简洁高效的策略，可从易得的芳基或杂环芳基甲基酮、吡啶和丙烯腈合成吲哚啉衍生物。机理途径涉及碘化、吡啶铵叶立德合成和1,3-二极环加成的整合。该方案在高产率、操作简便、温和反应条件和易于操作等方面表现出高效性。这种方法为通过新颖串联合成合成吲哚啉衍生物提供了重要补充。
• Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy
  作者：Qun Cai、Mei-Cai Liu、Bi-Ming Mao、Xuan Xie、Feng-Cheng Jia、Yan-Ping Zhu、An-Xin Wu

  DOI：10.1016/j.cclet.2014.12.016

  日期：2015.7

  2-a]pyridines from easily available starting materials: Aromatic ketones, α,β-unsaturated ketones, β-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined

  摘要建立了一种有效的一锅合成方案，用于从容易获得的起始原料：芳族酮，α，β-不饱和酮，β-酮酸酯和2-氨基吡啶合成咪唑并[1,2-a]吡啶。在I 2 / CuO的介质下，本反应在MeOH中进行得很好。通过使用这种方法，可以容易地以95％的收率制备市售药物zolimidine。所有这些目标产物均通过NMR，HRMS和IR光谱进行了表征。此外，通过X射线晶体学分析确定目标化合物3fa。
• Mild and General Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinolines and Related Polyheterocyclic Frameworks from Pyrrole Precursors Derived from a Mechanochemical Multicomponent Reaction
  作者：Marco Leonardi、Mercedes Villacampa、J. Carlos Menéndez

  DOI：10.1021/acs.joc.6b02995

  日期：2017.3.3

  synthesis performed under mechanochemical conditions with a TMSOTf-catalyzed oxonium-mediated cyclization gave general access to pyrrolo[2,1-a]isoquinoline derivatives under very mild conditions. The structural diversity generated by this method was extended by the preparation of six additional unusual polyheterocyclic frameworks.

  在机械化学条件下进行的三组分，无溶剂吡咯合成与TMSOTf催化的氧鎓介导的环化反应的结合，可在非常温和的条件下获得吡咯并[2,1- a ]异喹啉衍生物。这种方法产生的结构多样性通过另外六个非常规多杂环骨架的制备得以扩展。
• A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions
  作者：Zhihui Wang、Lei Wang、Zhiming Wang、Pinhua Li、Yicheng Zhang

  DOI：10.1016/j.cclet.2020.02.022

  日期：2021.1

  Abstract A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation

  摘要建立了在可见光条件下由烯烃合成α-溴/碘/氯酮的实用方法。在存在PhI（OAc）2作为促进剂的情况下，并且在环境条件下，苯乙烯和三碘甲烷的反应平稳地进行转化，从而在阳光照射下以良好的收率顺利地递送了相应的α-碘酮，而没有额外的光催化剂。同时，通过使用Ru（bpy）3Cl2作为光催化剂在蓝色LED（450-455 nm）辐射下，苯乙烯与三溴甲烷和三氯甲烷的反应可以高产率产生所需的α-溴代酮和α-氯代酮。