5-chloro-2(2-phenylethynyl)benzaldehyde oxime | 1260404-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-2(2-phenylethynyl)benzaldehyde oxime
• 英文别名: N-[[5-chloro-2-(2-phenylethynyl)phenyl]methylidene]hydroxylamine
• CAS: 1260404-60-1
• 化学式: C₁₅H₁₀ClNO
• 分子量: 255.703
• InChiKey: BTONDJGBNRCFQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2(2-phenylethynyl)benzaldehyde oxime 在 三乙烯二胺 、 oxone||potassium monopersulfate triple salt 、 sodium iodide 作用下， 以 水 为溶剂， 反应 20.0h， 生成 1-(7-chloro-4-iodo-3-phenylisoquinolin-1-yl)-1,3-di-p-tolylurea
  参考文献：
  名称：

  Facile assembly of 1-(4-haloisoquinolin-1-yl)ureas via a reaction of 2-alkynylbenzaldoxime, carbodiimide, and halide in water

  摘要：

  1-(4-Haloisoquinolin-1-yl)ureas are generated efficiently via a tandem reaction of 2-allcynylbenzal doxime, carbodiimide, with halide in water. The process involves the generation of halonium ion in situ by employment of Nal/oxone or NaBr/oxone as the promoters. This green process proceeds smoothly and efficiently, accommodating a variety of substituents to generate the desired products. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.026

文献信息

• An approach to 1-phosphorylated isoquinolines through silver(I)-catalyzed tandem reaction involving C–N and C–P bond formation
  作者：Xianbo Wang、Zhiyong Wang

  DOI：10.1016/j.tet.2014.06.060

  日期：2014.9

  A novel silver-catalyzed tandem reaction of 2-alkynylbenzaldoximes with H-phosphinate esters, and H-phosphine oxides has been developed, providing a general and powerful tool for the synthesis of various 1-phosphorylated isoquinolins in moderate to excellent yield. This reaction proceeded smoothly to construct C–N and C–P bonds in one-pot with good functional group tolerance under mild conditions.

  已开发出一种新颖的银催化的2-炔基苯甲肟与H-次膦酸酯和H-膦氧化物的串联反应，为合成各种1-磷酸化的异喹啉类化合物提供了通用而有效的工具，产率中等至优异。该反应顺利进行，在温和条件下，在一个罐中构建具有良好官能团耐受性的C–N和C–P键。
• A silver(I)-catalyzed reaction of 2-alkynylbenzaldoxime with arylsulfonyl chloride
  作者：Jinming Yang、Qing Xiao、Jie Sheng、Jie Wu

  DOI：10.1016/j.tet.2013.11.056

  日期：2014.1

  A silver-catalyzed reaction of 2-alkynylbenzaldoxime with arylsulfonyl chloride proceeds smoothly at room temperature to afford 4-tosyloxyisoquinolines in moderate to good yields. Additionally, the resulting 4-tosyloxyisoquinolines could be further elaborated through palladium-catalyzed coupling reactions leading to diverse isoquinolines.

  2-炔基苯甲恶肟与芳基磺酰氯的银催化反应在室温下平稳进行，以中等至良好的收率得到4-甲苯磺酰氧基异喹啉。另外，所得的4-甲苯磺酰氧基异喹啉可以通过钯催化的偶联反应进一步修饰，从而导致多种异喹啉。
• 1-(Isoquinolin-1-yl)urea Library Generation via Three-Component Reaction of 2-Alkynylbenzaldoxime, Carbodiimide, with Electrophile
  作者：Shengqing Ye、Huanhuan Wang、Jie Wu

  DOI：10.1021/co100026y

  日期：2011.3.14

  A novel and highly efficient three-component reaction of 2-alkynylbenzaldoxime, carbodiimide, with electrophile (bromine or iodine monochloride) is disclosed, which generates 1-(4-haloisoquinolin-1-yl)ureas in good yields under mild conditions. Subsequent palladium-catalyzed Suzuki−Miyaura coupling reaction is introduced, leading to the diverse 1-(isoquinolin-1-yl)ureas.

  公开了2-炔基苯甲肟，碳二亚胺与亲电试剂（溴或一氯化碘）的新颖且高效的三组分反应，其在温和条件下以高收率产生1-（4-卤代异喹啉-1-基）脲。随后引入了钯催化的Suzuki-Miyaura偶联反应，从而产生了多种1-（异喹啉-1-基）脲。
• Facile Synthesis of 1-(Isoquinolin-1-yl)ureas by Silver Triflate Catalyzed Tandem Reactions of 2-Alkynylbenzaldoximes with Carbodiimides
  作者：Shengqing Ye、Huanhuan Wang、Jie Wu

  DOI：10.1002/ejoc.201001040

  日期：2010.11

  2-Alkynylbenzaldoximes react with carbodiimides under mild conditions and silver triflate catalysis in DMF, leading to a diverse range of 1-(isoquinolin-1-yl)ureas in good to excellent yields. This transformation involves tandem 6-endo cyclization, [3+2] cycloaddition, and subsequent rearrangement.

  2-炔基苯甲醛肟在温和条件下与碳二亚胺反应，并在 DMF 中三氟甲磺酸银催化下，产生多种 1-（异喹啉-1-基）脲，产率从良好到极好。这种转化涉及串联 6-内环化、[3+2] 环加成和随后的重排。
• Generation of 1-aroxyisoquinolines via a silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol in the presence of p -toluenesulfonyl chloride
  作者：Qing Xiao、Danqing Zheng、Qiuping Ding、Jie Wu

  DOI：10.1016/j.tet.2013.04.076

  日期：2013.6

  A silver-catalyzed reaction of 2-alkynylbenzaldoxime with phenol promoted by p-toluenesulfonyl chloride leads to 1-aroxyisoquinolines in good yields. The presence of p-toluenesulfonyl chloride as an activator is essential for the successful transformation.

  银的2-炔基苯甲肟与由对甲苯磺酰氯促进的苯酚的银催化反应以良好的收率产生1-芳氧基异喹啉。存在p甲苯磺酰氯作为活化剂是成功转化是必需的。