1-(2-Iodoanilino)pentan-3-one | 501346-96-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-Iodoanilino)pentan-3-one
• CAS: 501346-96-9
• 化学式: C₁₁H₁₄INO
• 分子量: 303.143
• InChiKey: RACYPXOOMPSWRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-(2-Iodoanilino)pentan-3-one 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 caesium carbonate 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 96.0h， 生成 1-benzyl-4-ethyl-1,2,3,4-tetrahydro-4-quinolinol
  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 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 120.0h， 生成 1-(2-Iodoanilino)pentan-3-one
  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

文献信息

• 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。