1-(bromo-ethynyl)-3-methyl-benzene | 33675-43-3

• 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: 1-(bromo-ethynyl)-3-methyl-benzene
• 英文别名: 3-methylphenylacetylene bromide；Benzene, 1-(2-bromoethynyl)-3-methyl-；1-(2-bromoethynyl)-3-methylbenzene
• CAS: 33675-43-3
• 化学式: C₉H₇Br
• 分子量: 195.059
• InChiKey: HKFWAINXGQAMMO-UHFFFAOYSA-N

物化性质

• 沸点：
  246.3±33.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(bromo-ethynyl)-3-methyl-benzene 在 potassium iodide 作用下， 以 乙酸酐 为溶剂， 反应 6.0h， 以90%的产率得到1-((Z)-2-bromo-1-iodovinyl)-3-methylbenzene
  参考文献：
  名称：

  从末端炔烃高效合成两步合成（Z）-2-卤-1-碘代烯烃

  摘要：

  易于获得的卤代炔可以高产率转化为（Z）-2-卤-1-碘代烯烃，具有出色的区域和立体选择性。该方法显示出良好的官能团相容性。最终的产品可以找到广泛的应用。

  DOI：

  10.1039/c0cc02156c
• 作为产物：
  描述：

  1-(2,2-二溴乙烯基)-3-甲基苯 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-(bromo-ethynyl)-3-methyl-benzene
  参考文献：
  名称：

  Synthesis of heteroaryl ketones via tandem reaction of 1,1-dibromoethenes

  摘要：

  A novel method for the synthesis of heteroaryl ketones through one-pot tandem reaction of 1,1-dibromoethenes with 2-amino(thio)phenols promoted by TBAF center dot 3H(2)O and RuCl3(5%)/air was developed. This novel method includes several reactions in one-pot and utilizes economical yet efficient reagents to generate synthetically and biologically interesting heteroaryl ketones under mild conditions with good efficiency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.111

文献信息

• Brønsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo‐ and Enantioselective Synthesis of Spirolactams
  作者：Peng‐Fei Chen、Bo Zhou、Peng Wu、Binju Wang、Long‐Wu Ye

  DOI：10.1002/anie.202113464

  日期：2021.12.20

  A Brønsted acid catalyzed intramolecular hydroalkoxylation/Claisen rearrangement is disclosed that involves an unexpected dearomatization of nonactivated arenes and heteroaromatic compounds and allows the practical and atom-economic synthesis of various valuable spirolactams. Moreover, the asymmetric version of this tandem cyclization is also achieved via kinetic resolution by chiral phosphoric acid

  公开了布朗斯台德酸催化的分子内加氢烷氧基化/克莱森重排，其涉及未活化的芳烃和杂芳族化合物的意外脱芳构化，并允许各种有价值的螺内酰胺的实用和原子经济合成。此外，这种串联环化的不对称形式也是通过手性磷酸催化的动力学拆分来实现的。
• Metal-free hydration of aromatic haloalkynes to α-halomethyl ketones
  作者：Min Ye、Yuelu Wen、Huifang Li、Yejuan Fu、Qinghao Wang

  DOI：10.1016/j.tetlet.2016.09.088

  日期：2016.11

  A highly regioselective and efficient metal-free hydration of aromatic haloalkynes to α-halomethyl ketones using cheap tetrafluoroboric acid as catalyst is described. The protocol is conducted under convenient conditions and affords products in good to excellent yields, with broad substrate scope, including a variety of aromatic alkynyl chlorides, alkynyl bromides, and alkynyl iodides.

  描述了使用廉价的四氟硼酸作为催化剂的芳香族卤代炔烃的高度区域选择性和有效的无金属水合为α-卤代甲基酮。该方案是在方便的条件下进行的，并以良好的收率提供优良的产品，具有广泛的底物范围，包括各种芳族炔基氯，炔基溴化物和炔基碘化物。
• Gold(<scp>iii</scp>)-catalyzed chemoselective annulations of anthranils with <i>N</i>-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines
  作者：Lina Song、Xianhai Tian、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1039/c9cc04027g

  日期：——

  We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions.

  我们在此报告了在温和条件下金(III)催化的选择性闭环反应，即苯并噻唑与N-烯丙基亚胺的环化。
• First Catalyzed Hydration of Halo­alkynes by a Recyclable Catalytic ­System
  作者：Huaxu Zou、Weibao He、Qizhi Dong、Ruijia Wang、Niannian Yi、Jun Jiang、Dongming Pen、Weimin He

  DOI：10.1002/ejoc.201501198

  日期：2016.1

  The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also

  基于 Cu(OAc)2 催化剂和 TFA（三氟乙酸）促进剂的组合，卤代炔烃水合生成 α-卤代甲基酮。这是首次通过可回收催化系统催化的水合反应合成氯/溴/碘甲基酮。该催化体系具有广泛的底物范围和优异的化学选择性，并且该程序还可以按比例放大。
• Visible-Light-Promoted Oxidative Amidation of Bromoalkynes with Anilines: An Approach to α-Ketoamides
  作者：Ke Ni、Ling-Guo Meng、Kuai Wang、Lei Wang

  DOI：10.1021/acs.orglett.8b00586

  日期：2018.4.20

  A convenient and practical synthetic route to α-ketoamides from bromoalkynes and anilines through phototriggered organic transformations via a C–N cross-coupling and an oxidation of C≡C was developed. The reaction could be furnished without an external photocatalyst at ambient conditions, and a wide range of α-ketoamides were obtained in good yields.

  通过溴化炔和苯胺的光触发有机转化，通过C–N交叉偶联和C≡C的氧化，获得了一种方便实用的合成途径。在环境条件下可以在没有外部光催化剂的情况下提供反应，并且以良好的产率获得了多种α-酮酰胺。