1-(溴乙炔基)-3,5-双(三氟甲基)苯 | 1246224-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(溴乙炔基)-3,5-双(三氟甲基)苯
• 英文名称: 1-(bromoethynyl)-3,5-bis(trifluoromethyl)benzene
• 英文别名: 1-(2-bromoethynyl)-3,5-bis(trifluoromethyl)benzene
• CAS: 1246224-45-2
• 化学式: C₁₀H₃BrF₆
• 分子量: 317.028
• InChiKey: AQGQLTGCIOVLOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  222.1±50.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(溴乙炔基)-3,5-双(三氟甲基)苯 在 水 、 silver fluoride 、 三氟乙酸 作用下， 反应 6.0h， 以78%的产率得到尼麦角林杂质D
  参考文献：
  名称：

  AgF/TFA-promoted highly efficient synthesis of α-haloketones from haloalkynes

  摘要：

  A AgF/TFA-promoted highly efficient synthesis of a wide range of alpha-haloketones from haloalkynes is described. The reactions are conducted under convenient conditions and provide products in moderate to excellent yields, with broad substrate scope, including a variety of aromatic chloroalkynes and bromoalkynes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.027
• 作为产物：
  描述：

  3,5-双三氟甲基苯乙炔 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 1-(溴乙炔基)-3,5-双(三氟甲基)苯
  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

文献信息

• Cross-coupling of 1,1-difluoro-1-en-3-yn-2-yl tosylates with arylboronic acids: A new approach to 2-aryl-1,1-difluoro-1,3-enynes
  作者：Su Jin Kim、Hyun Gyu Ryu、Sung Lan Jeon、In Howa Jeong

  DOI：10.1016/j.jfluchem.2016.08.014

  日期：2017.4

  The palladium-catalyzed direct alkynylation of 2,2-difluoro-1-tributylstannylethenyl p-toluenesulfonate 1 with alkynyl bromides provided the corresponding 1,1-difluoro-1,3-enynyl tosylates 2 in good yields. The Suzuki-Miyaura arylation reaction of 2 with arylboronic acids afforded the cross-coupled products, 2-aryl-1,1-difluoro-1,3-enynes 3, in good yields.

  2,2-二氟-1- tributylstannylethenyl的钯催化的直接炔基p甲苯磺酸盐1与炔基溴化物提供相应的1,1-二氟-1,3- enynyl甲苯磺酸酯2以良好的收率。2与芳基硼酸的Suzuki-Miyaura芳基化反应以高收率提供了交联产物2-芳基-1,1-二氟-1,3-烯炔3。
• Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution
  作者：Mikk Kaasik、Sandra Kaabel、Kadri Kriis、Ivar Järving、Riina Aav、Kari Rissanen、Tõnis Kanger

  DOI：10.1002/chem.201700618

  日期：2017.5.29

  A general platform for the synthesis of various chiral halogen‐bond (XB) donors based on the triazole core and the characterisation of factors that influence the strength of the halogen bond in the solid state and in solution are reported. The characterisation of XB donors in the solid state by X‐ray crystallography and in solution by 1H NMR titration can be used to aid the design of new XB donors

  报告了基于三唑核合成各种手性卤素键（XB）供体的通用平台，并描述了影响固态和溶液中卤素键强度的因素的表征。通过X射线晶体学表征溶液中的​​XB供体，通过1 H NMR滴定表征溶液中的​​XB供体，可用于设计新的XB供体。我们描述了溶液中碘代三唑和硫脲之间XB的第一个例子。此外，还描述了通过卤素键参与的溶液中受体的对映异构。
• Transition-Metal-Free Homocoupling of 1-Haloalkynes: A Facile Synthesis of Symmetrical 1,3-Diynes
  作者：Zhengwang Chen、Huanfeng Jiang、Azhong Wang、Shaorong Yang

  DOI：10.1021/jo101216m

  日期：2010.10.1

  Symmetrical 1,3-diyne compounds can be easily synthesized via a transition-metal-free homocoupling reaction of 1-haloalkynes without base and oxidant. The method shows excellent functional group compatibility and high yields.

  对称的1,3-二炔化合物可以通过1-卤代炔烃的无过渡金属无均相偶联反应轻松合成，而无需碱和氧化剂。该方法显示出优异的官能团相容性和高产率。
• Visible-Light-Mediated Deacylated Alkynylation of Unstrained Ketone
  作者：Hao Wu、Shuguang Chen、Dengmengfei Xiao、Feng Li、Kaiyuan Zhou、Xiaocui Yin、Chunni Liu、Xinwei He、Yongjia Shang

  DOI：10.1021/acs.orglett.3c00145

  日期：2023.2.24

  Deconstructive alkynylation of an unstrained ketone catalyzed by an organic photocatalyst under blue light irradiation is reported for the first time. A broad substrate scope with up to 63 examples, excellent functional group tolerance, and gram scale reaction demonstrated the practicality of this novel alkynylation method. The dihydroquinazolinone derivative of trifluoroacetophenone had been proved

  首次报道了在蓝光照射下由有机光催化剂催化的未应变酮的解构炔基化。具有多达 63 个实例的广泛底物范围、出色的官能团耐受性和克级反应证明了这种新型炔基化方法的实用性。三氟苯乙酮的二氢喹唑啉酮衍生物在与各种炔基溴化物的三氟甲基化反应中表现良好，已被证明具有作为新型三氟甲基化试剂的潜力。
• Practical synthesis of amides from alkynyl bromides, amines, and water
  作者：Zheng-Wang Chen、Huan-Feng Jiang、Xiao-Yan Pan、Zai-Jun He

  DOI：10.1016/j.tet.2011.06.045

  日期：2011.8

  A general and efficient method for the synthesis of a wide range of amides is described here. The reactions were conducted under convenient conditions and provided secondary and tertiary amides in moderate to excellent yields. A variety of amines and substituted alkynyl bromides were used to investigate the scope of the reactions. (C) 2011 Elsevier Ltd. All rights reserved.