(E)-1-(2-nitrovinyl)-2-(phenylethynyl)benzene | 1352832-01-9

• 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)-1-(2-nitrovinyl)-2-(phenylethynyl)benzene
• 英文别名: 1-[(E)-2-nitroethenyl]-2-(2-phenylethynyl)benzene
• CAS: 1352832-01-9
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: RPRNNRWOLPOBHL-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-nitrovinyl)-2-(phenylethynyl)benzene 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以88%的产率得到5-phenyl-[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：

  在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以4.48 g的产率得到(E)-1-(2-nitrovinyl)-2-(phenylethynyl)benzene
  参考文献：
  名称：

  合并有机催化和金催化：通过顺序双Friedel-Crafts型反应的四环吲哚衍生物的对映选择性合成

  摘要：

  另一个吲哚奇迹：在C2，C3未取代的吲哚上有机催化和金催化的顺序结合提供了有效的一锅式获得四环吲哚衍生物的方法，产率很高，对映选择性极好（参见方案）。双弗里德尔-克拉夫茨型反应，其中包括一种罕见的7-内切-挖环化，打开一个新的项，以对映体富集的高度抗癌药物，如DNA嵌入。

  DOI：

  10.1002/chem.201102793

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。
• The Chameleonic Nature of the Nitro Group Applied to a Base-Promoted Cascade Reaction To Afford Indane-Fused Dihydrofurans
  作者：Howard Díaz-Salazar、Juan Carlos Rodríguez-Colín、Josué Vazquez-Chavez、Marcos Hernández-Rodríguez

  DOI：10.1021/acs.joc.3c00132

  日期：2023.7.7

  Michael/Conia-ene/SN2 cascade reaction for the synthesis of Indane-fused dihydrofurans from 1,3-dicarbonyl compounds and 2-alkynylnitrostyrenes promoted by potassium carbonate in DMSO at room temperature. In this reaction, the nitro group has a chameleonic role, first as an electron-withdrawing group for the Michael addition, then the nitronate behaves as a nucleophile, and finally, the allylic nitro acts as a

  我们公开了在室温下在DMSO中碳酸钾促进下由1,3-二羰基化合物和2-炔基硝基苯乙烯合成茚满稠合二氢呋喃的Michael/Conia-ene/S N 2 级联反应。在该反应中，硝基具有变色作用，首先作为迈克尔加成的吸电子基团，然后硝基充当亲核试剂，最后，烯丙基硝基充当离去基团。该产品以单一非对映异构体形式获得，其中 1,3-酮酯含量高达 82%，1,3-二酮含量高达 58%。此外，反应机理的 DFT 计算解释了硝基化合物在烯醇化物上化学选择性加成到未活化的三键上，烯醇化物的加成是高度吸热的。
• Merging Organocatalysis and Gold Catalysis: Enantioselective Synthesis of Tetracyclic Indole Derivatives through a Sequential Double Friedel-Crafts Type Reaction
  作者：Charles C. J. Loh、Jan Badorrek、Gerhard Raabe、Dieter Enders

  DOI：10.1002/chem.201102793

  日期：2011.11.25

  Yet another indole miracle: The sequential combination of organocatalysis and gold catalysis on C2,C3‐unsubstituted indoles provides an efficient one‐pot access to tetracyclic indole derivatives in very good yields and excellent enantioselectivities (see scheme). The double Friedel–Crafts type reaction, including a rare 7‐endo‐dig cyclisation, opens a new entry to highly enantioenriched anticancer

  另一个吲哚奇迹：在C2，C3未取代的吲哚上有机催化和金催化的顺序结合提供了有效的一锅式获得四环吲哚衍生物的方法，产率很高，对映选择性极好（参见方案）。双弗里德尔-克拉夫茨型反应，其中包括一种罕见的7-内切-挖环化，打开一个新的项，以对映体富集的高度抗癌药物，如DNA嵌入。
• 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.