2-(2-nitro-6-methylphenyl)-1,1-dichloroethylene | 1353714-58-5

• 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-nitro-6-methylphenyl)-1,1-dichloroethylene
• CAS: 1353714-58-5
• 化学式: C₉H₇Cl₂NO₂
• 分子量: 232.066
• InChiKey: VSWVMAVGVVQCMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2-nitro-6-methylphenyl)-1,1-dichloroethylene 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以2.372 g的产率得到2-(2-Chloroethynyl)-1-methyl-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
• 作为产物：
  描述：

  3-硝基邻二甲苯 在 sodium periodate 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 2-(2-nitro-6-methylphenyl)-1,1-dichloroethylene
  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