2-(2-Bromoethynyl)-1-chloro-3-nitrobenzene | 1353714-60-9

• 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: 2-(2-Bromoethynyl)-1-chloro-3-nitrobenzene
• CAS: 1353714-60-9
• 化学式: C₈H₃BrClNO₂
• 分子量: 260.474
• InChiKey: DIZPTYBREXYPHR-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  338.7±52.0 °C(predicted)
• 密度：
  1.82±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• 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：

  2-(2-Bromoethynyl)-1-chloro-3-nitrobenzene 、 2,4,6-trimethylbenzohydroximoyl chloride 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以68%的产率得到4-Bromo-5-(2-chloro-6-nitrophenyl)-3-(2,4,6-trimethylphenyl)-1,2-oxazole
  参考文献：
  名称：

  带有邻硝基苯基炔烃的区域选择性高的丁腈氧化偶极环加成†

  摘要：

  已证明邻硝基苯基炔烃与芳基腈氧化物的偶极环加成。炔烃上可容忍一系列取代基。这些反应以极好的区域选择性进行。已经证明了异恶唑支架的随后功能化。

  DOI：

  10.1039/c2ob26267c
• 作为产物：
  描述：

  2-氯-6-硝基苯甲醛 在 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.08h， 生成 2-(2-Bromoethynyl)-1-chloro-3-nitrobenzene
  参考文献：
  名称：

  Synthesis and Computational Analysis of Densely Functionalized Triazoles Using o-Nitrophenylalkynes

  摘要：

  Dipolar cylcoadditions with azides using a series of o-nitrophenylethynes and disubstituted alkynes were studied experimentally and computationally. Density functional theory computations reveal the steric and electronic parameters that control the regioselectivity of these cycloadditions. Several new substrates were predicted that would either give enhanced regiocontrol or invert the regiochemical preference. Experimentally, the alkynes were screened in the [3 + 2] cycloaddition with benzyl azide. Of the 11 alkynes screened experimentally, the acetylenes containing halogen substitution directly on the alkyne provided the highest levels of regioselectivity. These haloalkynes were also shown to tolerate variation of the azide moiety with continued good levels of regioselectivity in most cases. Diverse functional groups can be incorporated through the cycloaddition process and their subsequent orthogonal modification was demonstrated.

  DOI：

  10.1021/jo202467k

文献信息

• Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes
  作者：Melissa L. McIntosh、Michael R. Naffziger、Bradley O. Ashburn、Lev N. Zakharov、Rich G. Carter

  DOI：10.1039/c2ob26267c

  日期：——

  The dipolar cycloadditions of ortho-nitrophenyl alkynes with aryl nitrile oxides has been demonstrated. A range of substituents are tolerated on the alkyne. These reactions proceed with excellent levels of regioselectivity. Subsequent functionalization of the isoxazole scaffold has been demonstrated.

  已证明邻硝基苯基炔烃与芳基腈氧化物的偶极环加成。炔烃上可容忍一系列取代基。这些反应以极好的区域选择性进行。已经证明了异恶唑支架的随后功能化。
• Synthesis and Computational Analysis of Densely Functionalized Triazoles Using <i>o</i>-Nitrophenylalkynes
  作者：Melissa L. McIntosh、Ryne C. Johnston、Ommidala Pattawong、Bradley O. Ashburn、Michael R. Naffziger、Paul Ha-Yeon Cheong、Rich G. Carter

  DOI：10.1021/jo202467k

  日期：2012.1.20

  Dipolar cylcoadditions with azides using a series of o-nitrophenylethynes and disubstituted alkynes were studied experimentally and computationally. Density functional theory computations reveal the steric and electronic parameters that control the regioselectivity of these cycloadditions. Several new substrates were predicted that would either give enhanced regiocontrol or invert the regiochemical preference. Experimentally, the alkynes were screened in the [3 + 2] cycloaddition with benzyl azide. Of the 11 alkynes screened experimentally, the acetylenes containing halogen substitution directly on the alkyne provided the highest levels of regioselectivity. These haloalkynes were also shown to tolerate variation of the azide moiety with continued good levels of regioselectivity in most cases. Diverse functional groups can be incorporated through the cycloaddition process and their subsequent orthogonal modification was demonstrated.