1,2-双(3-硝基苯基)乙烯 | 20657-40-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1,2-双(3-硝基苯基)乙烯
• 英文名称: cis-4,4'-dinitrostilbene
• 英文别名: 1-nitro-3-[(Z)-2-(3-nitrophenyl)ethenyl]benzene
• CAS: 20657-40-3
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: DUTMIVLDFHVUNY-FPLPWBNLSA-N

物化性质

• 沸点：
  433.6±34.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-双(3-硝基苯基)乙烯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 2,3-bis-(3-nitro-phenyl)-oxirane
  参考文献：
  名称：

  Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol-titanium complex

  摘要：

  This study describes a C-2-symmetric ligand comprising a central bipyridine-pinene-derived core and two functionalized diphenylmethanol subunits. [8 '-(Hydroxy-diphenyl-methyl)-10,10,10 ',10 '-tetramethyl-[5,5']bi[6-aza-tricyclo[7.1.1.0(2,7) ]undecyl]-2(7),3,5, 2 '(7 '),3 ',5 '-hexaen-8-yl]-diphenyl-methanol 1 is an effective catalyst in the asymmetric ring opening (ARO) of ineso-epoxides with PhSH and inductions of up to 69% ee. Importantly, there was a correlation between Hammett substituent constants and enantiomeric excesses; the electron-donating substituents at the meta- and para-positions of the substituted stilbene oxides had good enantioselectivity during the epoxide ring opening using PhSH. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.030
• 作为产物：
  描述：

  间硝基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 1,2-双(3-硝基苯基)乙烯
  参考文献：
  名称：

  Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol-titanium complex

  摘要：

  This study describes a C-2-symmetric ligand comprising a central bipyridine-pinene-derived core and two functionalized diphenylmethanol subunits. [8 '-(Hydroxy-diphenyl-methyl)-10,10,10 ',10 '-tetramethyl-[5,5']bi[6-aza-tricyclo[7.1.1.0(2,7) ]undecyl]-2(7),3,5, 2 '(7 '),3 ',5 '-hexaen-8-yl]-diphenyl-methanol 1 is an effective catalyst in the asymmetric ring opening (ARO) of ineso-epoxides with PhSH and inductions of up to 69% ee. Importantly, there was a correlation between Hammett substituent constants and enantiomeric excesses; the electron-donating substituents at the meta- and para-positions of the substituted stilbene oxides had good enantioselectivity during the epoxide ring opening using PhSH. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.030

文献信息

• Libraries for Receptor-Assisted Combinatorial Synthesis (RACS). The Olefin Metathesis Reaction
  作者：Thomas Giger、Maria Wigger、Stephan Audétat、Steven A. Benner

  DOI：10.1055/s-1998-1737

  日期：1998.6

  A library of alkenes is generated using the olefin metathesis reaction, and converted to a set of diols suitable for a receptor assisted combinatorial synthesis (RACS) experiment with borate as a linker.

  通过烯烃交叉反应生成了一系列烯烃库，并将其转化为一组适合于受体辅助组合合成（RACS）实验的二醇，硼酸盐作为连接体。
• Iodine atom-catalysed isomerisation of symmetrically substituted cis-stilbenes
  作者：W. J. Muizebelt、R. J. F. Nivard

  DOI：10.1039/j29680000913

  日期：——

  19 symmetrically substituted cis-stilbenes between 70 and 120°. The reaction rate is of the first order in cis-stilbene derivative and of half order with respect to iodine, which indicates that iodine atoms are the catalytic species. For most compounds value of log k fit a Hammett relation with a negative ρ-value, which can be explained on the basis of the electrophilic character on the iodine atom

  已经测量了碘在70到120°之间由碘催化的19个对称取代的顺式-苯乙烯衍生物的顺式-反式异构化的速率常数。反应速率是顺式-二苯乙烯衍生物的一级，并且是相对于碘的一半，这表明碘原子是催化物质。对于大多数化合物，log k的值拟合一个具有负ρ值的Hammett关系，这可以根据碘原子的亲电特性来解释。一些对位取代的顺式β-苯乙烯衍生物偏离哈米特谱线，显然是因为在这些情况下，作为中间体形成的苄基自由基具有额外的共振稳定性，因此降低了过渡态的能量。在这方面，在异构化和均相苯基化之间发现平行。
• Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol-titanium complex
  作者：Yi-Jing Chen、Chinpiao Chen

  DOI：10.1016/j.tetasy.2007.04.030

  日期：2007.6

  This study describes a C-2-symmetric ligand comprising a central bipyridine-pinene-derived core and two functionalized diphenylmethanol subunits. [8 '-(Hydroxy-diphenyl-methyl)-10,10,10 ',10 '-tetramethyl-[5,5']bi[6-aza-tricyclo[7.1.1.0(2,7) ]undecyl]-2(7),3,5, 2 '(7 '),3 ',5 '-hexaen-8-yl]-diphenyl-methanol 1 is an effective catalyst in the asymmetric ring opening (ARO) of ineso-epoxides with PhSH and inductions of up to 69% ee. Importantly, there was a correlation between Hammett substituent constants and enantiomeric excesses; the electron-donating substituents at the meta- and para-positions of the substituted stilbene oxides had good enantioselectivity during the epoxide ring opening using PhSH. (c) 2007 Elsevier Ltd. All rights reserved.