反式-1,2-二氰基-1,2-双(3-甲氧基苯基)乙烯 | 67705-33-3

• 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: 反式-1,2-二氰基-1,2-双(3-甲氧基苯基)乙烯
• 英文名称: trans-1,2-Dicyano-1,2-bis(3-methoxyphenyl)ethylene
• 英文别名: 1,2-Dicyano-1,2-di-(3'-methoxyphenyl)ethylene；(E)-2,3-bis(3-methoxyphenyl)but-2-enedinitrile
• CAS: 67705-33-3
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: GAXBMZCLUPGQEP-ISLYRVAYSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  445.7±45.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基苯乙腈 在 正丁基锂 、 溴五氟苯 作用下， 以27%的产率得到反式-1,2-二氰基-1,2-双(3-甲氧基苯基)乙烯
  参考文献：
  名称：

  溴五氟苯和五氟苯基锂与α-锂化的芳基乙腈的反应

  摘要：

  溴五氟苯和五氟苯基锂在醚中与α-锂化的芳基乙腈反应，分别得到α-芳基-2,3,5,6-四氟苯基乙腈和α-芳基-4-溴-2,3,5,6-四氟苯基乙腈。然而，溴五氟苯与α-锂化的芳基乙腈在乙醚/ THF中的反应提供了反式-1，2-二氰基苯乙烯基苯。提出了形成各种产物的机制。

  DOI：

  10.1016/0022-1139(95)03351-3

文献信息

• Reaction of Hexachlorobenzene and (Pentachlorophenyl)lithium with .alpha.-Arylacetonitriles
  作者：Hala Mohammed Refat、John Waggenspack、Mahesh Dutt、Hongming Zhang、A. A. Fadda、Ed Biehl

  DOI：10.1021/jo00112a019

  日期：1995.4

  (Pentachlorophenyl)lithium (2) reacts with alpha-lithio-alpha-arylacetonitriles (4) at -70 degrees C to room temperature to supply alpha-aryl-alpha-(2,3,5,6-tetrachlorophenyl)ace a. Small amounts of 1,2,4,5-tetrachlorobenzene (8) and trans-1,2-dicyano-1,2-diarylethylenes 9 are also obtained; however, no alpha-tetrachloroarylated nitriles 6 from 3,4,5,6-tetrachlorobenzyne were detected. Similar treatment of hexachlorobenzene (1) and 4 afforded alpha-aryl-alpha-(2,3,4,5,6-pentachlorophenyl)acetonitriles 10. The addition of 2 to 4 at tetrachlorobenzyne-generating temperatures (0-20 degrees C) gave a complex mixture containing mainly dimeric and polymeric materials; 6 was not found. A mechanism is proposed for the reaction of 2 and 4 which suggests that nitriles 7 are formed by the condensation of 2 and 4 via a four-centered transition state and that alkenes 9 are supplied by a base-mediated dimerization of alpha-chloro-alpha-arylacetonitriles 13, formed by a lithium-chlorine exchange between 2 and 4. Nitriles 10 most likely are provided from the reaction of 1 and 4 by the usual aromatic nucleophilic substitution pathway.
• POCHAT F., TETRAHEDRON LETT., 1978, NO 12, 1055-1058
  作者：POCHAT F.

  DOI：——

  日期：——
• Reaction of bromopentafluorobenzene and pentafluorophenyllithium with α-lithiated arylacetonitriles
  作者：Hala Mohammed Refat、Ahmed A. Faddo、Ed Biehl

  DOI：10.1016/0022-1139(95)03351-3

  日期：1996.1

  Bromopentafluorobenzene and pentafluorophenyllithium react with α-lithiated arylacetonitriles in ether to give α-aryl-2,3,5,6-tetrafluorophenylacetonitriles and α-aryl-4-bromo-2,3,5,6-tetrafluorophenylacetonitriles, respectively. However, the reaction of bromopentafluorobenzene with α-lithiated arylacetonitriles in ether/THF affords trans-1,2-dicyanostilbenes. Mechanisms for the formation of the various

  溴五氟苯和五氟苯基锂在醚中与α-锂化的芳基乙腈反应，分别得到α-芳基-2,3,5,6-四氟苯基乙腈和α-芳基-4-溴-2,3,5,6-四氟苯基乙腈。然而，溴五氟苯与α-锂化的芳基乙腈在乙醚/ THF中的反应提供了反式-1，2-二氰基苯乙烯基苯。提出了形成各种产物的机制。