N-[[5-fluoro-2-[2-(4-methoxyphenyl)ethynyl]phenyl]methylidene]hydroxylamine | 1095128-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[[5-fluoro-2-[2-(4-methoxyphenyl)ethynyl]phenyl]methylidene]hydroxylamine
• CAS: 1095128-61-2
• 化学式: C₁₆H₁₂FNO₂
• 分子量: 269.275
• InChiKey: BIGVXSYSCAYLQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[[5-fluoro-2-[2-(4-methoxyphenyl)ethynyl]phenyl]methylidene]hydroxylamine 、 N,N'-二异丙基碳二亚胺 在 silver trifluoromethanesulfonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到1-(7-fluoro-3-(4-methoxyphenyl)isoquinolin-1-yl)-1,3-diisopropylurea
  参考文献：
  名称：

  三氟甲磺酸银催化 2-炔基苯甲醛肟与碳二亚胺串联反应合成 1-(异喹啉-1-基)脲

  摘要：

  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。

  DOI：

  10.1002/ejoc.201001040

文献信息

• Multicatalytic Tandem Reactions of 2-Alkynylbenzaldoximes with Isocyanides
  作者：Zhiyuan Chen、Xingxin Yu、Mingchao Su、Xiaodi Yang、Jie Wu

  DOI：10.1002/adsc.200900442

  日期：2009.11

  An efficient tandem reaction of 2-alkynylbenzaldoximes with isocyanides co-catalyzed by silver triflate and bismuth triflate has been developed, which gives rise to the unexpected N-(isoquinolin-1-yl)formamides in good to excellent yields. The iodo- and bromo-containing products could be obtained as well by variation of the reaction conditions.

  已经开发了由三氟甲磺酸银和三氟甲磺酸铋共同催化的2-炔基苯甲肟与异氰酸酯的有效串联反应，从而产生了出人意料的高产N-（异喹啉-1-基）甲酰胺。通过改变反应条件也可以得到含碘和溴的产物。
• Tandem Electrophilic Cyclization−[3+2] Cycloaddition−Rearrangement Reactions of 2-Alkynylbenzaldoxime, DMAD, and Br₂
  作者：Qiuping Ding、Zhiyong Wang、Jie Wu

  DOI：10.1021/jo802076k

  日期：2009.1.16

  Tandem electrophilic cyclization-[3+2] cycloaddition -rearrangement reactions of 2-alkynylbenzaldoximes, DMAD, and bromine are described, which afford the unexpected isoquinoline-based azomethine ylides in good to excellent yields. The products could be further elaborated via palladium-catalyzed cross-coupling reactions to generate highly functionalized isoquinoline-based stable azomethine ylides.
• Tandem cyclization-[3+3] cycloaddition reactions of 2-alkynylbenzaldoxime: synthesis of fused 1,2-dihydroisoquinolines
  作者：Qiuping Ding、Zhiyong Wang、Jie Wu

  DOI：10.1016/j.tetlet.2008.10.121

  日期：2009.1

  Tandem cyclization-[3+3] cycloaddition of 2-alkynylbenzaldoximes with dimethyl cyclopropane-1,1-dicarboxylate co-catalyzed by AgOTf and Yb(OTf)(3) is described, which provides an useful method for the synthesis of tetrahydro-1,2-oxazine fused 1,2-dihydroisoquinolines. (C) 2008 Elsevier Ltd. All rights reserved.
• 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。