(E)-4-fluoro-2-(2-nitrovinyl)-1-(p-tolylethynyl)benzene | 1427018-06-1

• 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: (E)-4-fluoro-2-(2-nitrovinyl)-1-(p-tolylethynyl)benzene
• 英文别名: 4-fluoro-1-[2-(4-methylphenyl)ethynyl]-2-[(E)-2-nitroethenyl]benzene
• CAS: 1427018-06-1
• 化学式: C₁₇H₁₂FNO₂
• 分子量: 281.286
• InChiKey: JGZZUHKZCGRJLY-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-fluoro-2-(2-nitrovinyl)-1-(p-tolylethynyl)benzene 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以82%的产率得到9-fluoro-5-(4-methylphenyl)[1,2,3]triazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynylbenzaldehyde via Domino Reactions under Transition-Metal-Free Conditions

  摘要：

  We describe two simple straightforward syntheses of triazolo isoquinolines (3) and isochromenes (7) from 2-alkynylbenzaldehydes (1) as a common synthon. The synthetic strategy for 3 involves formation of the (E)-1-(2-nitrovinyl)-2-(alkynyl)benzene species 2 via condensation of synthon 1 with nitromethane followed by a [3 + 2] cycloaddition/extrusion of the nitro group/regioselective 6-endo cyclization domino sequence. In yet another strategy, the synthon 1 was condensed with nitromethane followed by electrophilic iodo cyclization of the resulting 2-nitro-1-(2-(alkynyl)phenyl)ethanol (6) to furnish iodo isochromene derivatives. The salient feature of the above two strategies involves formation of the corresponding heterocycles under metal-free conditions in good yields.

  DOI：

  10.1021/jo401929q
• 作为产物：
  描述：

  硝基甲烷 、 5-氟-2 -(甲基苯乙炔基)苯甲醛 在 ammonium acetate 作用下， 反应 1.0h， 生成 (E)-4-fluoro-2-(2-nitrovinyl)-1-(p-tolylethynyl)benzene
  参考文献：
  名称：

  Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynylbenzaldehyde via Domino Reactions under Transition-Metal-Free Conditions

  摘要：

  We describe two simple straightforward syntheses of triazolo isoquinolines (3) and isochromenes (7) from 2-alkynylbenzaldehydes (1) as a common synthon. The synthetic strategy for 3 involves formation of the (E)-1-(2-nitrovinyl)-2-(alkynyl)benzene species 2 via condensation of synthon 1 with nitromethane followed by a [3 + 2] cycloaddition/extrusion of the nitro group/regioselective 6-endo cyclization domino sequence. In yet another strategy, the synthon 1 was condensed with nitromethane followed by electrophilic iodo cyclization of the resulting 2-nitro-1-(2-(alkynyl)phenyl)ethanol (6) to furnish iodo isochromene derivatives. The salient feature of the above two strategies involves formation of the corresponding heterocycles under metal-free conditions in good yields.

  DOI：

  10.1021/jo401929q

文献信息

• Gold-catalyzed Michael addition/intramolecular annulation cascade: an effective pathway for the chemoselective- and regioselective synthesis of tetracyclic indole derivatives in water
  作者：Shengtao Xu、Yu Zhou、Jinyi Xu、Hualiang Jiang、Hong Liu

  DOI：10.1039/c2gc36301a

  日期：——

  The report describes a gold(I) complex and trifluoroacetic acid (TFA) cocatalyzed one-pot, Michael addition/intramolecular cyclization cascade reaction for the synthesis of unusual tetracyclic indoles containing a seven-membered ring in water with microwave irradiation (MW). This protocol presents an operationally simple, rapid and environmentally friendly strategy for preparing potential biologically

  该报告描述了一种金（I）配合物，三氟乙酸 （TFA）共催化一锅， 迈克尔加法/分子内 环化 级联反应合成不寻常的四环 吲哚 包含一个七元环 水微波辐射（兆瓦）。该协议提出了一种操作简单，快速且环境友好的策略，可用于制备潜在的生物学有趣的融合-吲哚 从一些简单的起始材料开始的分子结构。
• Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynylbenzaldehyde via Domino Reactions under Transition-Metal-Free Conditions
  作者：Rajesh K. Arigela、Srinivas Samala、Rohit Mahar、Sanjeev K. Shukla、Bijoy Kundu

  DOI：10.1021/jo401929q

  日期：2013.10.18

  We describe two simple straightforward syntheses of triazolo isoquinolines (3) and isochromenes (7) from 2-alkynylbenzaldehydes (1) as a common synthon. The synthetic strategy for 3 involves formation of the (E)-1-(2-nitrovinyl)-2-(alkynyl)benzene species 2 via condensation of synthon 1 with nitromethane followed by a [3 + 2] cycloaddition/extrusion of the nitro group/regioselective 6-endo cyclization domino sequence. In yet another strategy, the synthon 1 was condensed with nitromethane followed by electrophilic iodo cyclization of the resulting 2-nitro-1-(2-(alkynyl)phenyl)ethanol (6) to furnish iodo isochromene derivatives. The salient feature of the above two strategies involves formation of the corresponding heterocycles under metal-free conditions in good yields.