4-(2-iodophenylamino)-2-butanone | 163444-05-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(2-iodophenylamino)-2-butanone
• 英文别名: 4-[N-(2-iodophenyl)amino]-2-butanone；4-(2-iodophenylamino)butan-2-one；4-(2-Iodoanilino)butan-2-one；4-(2-iodoanilino)butan-2-one
• CAS: 163444-05-1
• 化学式: C₁₀H₁₂INO
• 分子量: 289.116
• InChiKey: XLAWOSBVBKCYKX-UHFFFAOYSA-N

物化性质

• 沸点：
  370.2±27.0 °C(Predicted)
• 密度：
  1.627±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-iodophenylamino)-2-butanone 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 27.0h， 生成 3-acetyl-1-(methoxycarbonyl)indole
  参考文献：
  名称：

  Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles

  摘要：

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.

  DOI：

  10.1021/ja029114w
• 作为产物：
  描述：

  2-碘苯胺 、 丁烯酮 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 4-(2-iodophenylamino)-2-butanone
  参考文献：
  名称：

  一锅金催化的叠氮基[1,2-a]吲哚的合成

  摘要：

  从零开始的吲哚：发现金（I）/ N-杂环卡宾络合物（IPr = 1,3-二（异丙基苯基）咪唑-2-亚烷基）特别有效，可一锅合成三环氮杂吲哚类化合物具有前所未有的级联反应。该方法的主要优点是易于获得的底物，高的化学选择性，良好的收率以及水是唯一的化学计量副产物。

  DOI：

  10.1002/anie.201205463

文献信息

• Green, efficient and practical Michael addition of arylamines to α,β-unsaturated ketones
  作者：Ran Jiang、Dan-Hua Li、Jing Jiang、Xiao-Ping Xu、Tao Chen、Shun-Jun Ji

  DOI：10.1016/j.tet.2011.03.082

  日期：2011.5

  The aza-Michael addition of aromatic amines to alpha,beta-unsaturated ketones was carried out effectively at room temperature in good to excellent yields without any catalyst or solvent. It was significant that part of adducts could be collected in almost quantitative yield without column chromatography. This procedure offered a green, efficient, and practical approach for the synthesis of beta-amino ketones. (C) 2011 Elsevier Ltd. All rights reserved.
• Amide-based protecting/radical translocating (PRT) groups. Generation of radicals adjacent to carbonyls by 1,5-hydrogen transfer reactions of o-iodoanilides
  作者：Dennis P. Curran、Hosung Yu、Hongtao Liu

  DOI：10.1016/s0040-4020(01)90466-1

  日期：——

  The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best ''protecting/radical translocating'' (PRT) groups introduced to date. Beyond its good performance in radical translocation reactions, it is easy to introduce, serves as a reasonable protecting group both before and after the translocation, and (with appropriate modifications) is easy to remove.
• Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles
  作者：Daniel Solé、Lluís Vallverdú、Xavier Solans、Mercè Font-Bardía、Josep Bonjoch

  DOI：10.1021/ja029114w

  日期：2003.2.1

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.
• One-Pot Gold-Catalyzed Synthesis of Azepino[1,2-<i>a</i>]indoles
  作者：Gianpiero Cera、Stefano Piscitelli、Michel Chiarucci、Giancarlo Fabrizi、Antonella Goggiamani、Rubén S. Ramón、Steven P. Nolan、Marco Bandini

  DOI：10.1002/anie.201205463

  日期：2012.9.24

  Indoles from scratch: A gold(I)/N‐heterocyclic carbene complex (IPr=1,3‐di(isopropylphenyl)imidazol‐2‐ylidene) was found to be particularly effective as a catalyst, enabling the one‐pot synthesis of tricyclic azepinoindoles by an unprecedented cascade reaction. Readily available substrates, high chemoselectivity, good yields, and water as the only stoichiometric by‐product are some of the main advantages

  从零开始的吲哚：发现金（I）/ N-杂环卡宾络合物（IPr = 1,3-二（异丙基苯基）咪唑-2-亚烷基）特别有效，可一锅合成三环氮杂吲哚类化合物具有前所未有的级联反应。该方法的主要优点是易于获得的底物，高的化学选择性，良好的收率以及水是唯一的化学计量副产物。