(Z)-(1-bromo-2-fluoroethene-1,2-diyl)dibenzene | 109084-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-(1-bromo-2-fluoroethene-1,2-diyl)dibenzene
• 英文别名: (Z)-1-bromo-2-fluoro-1,2-diphenylethene；Z-1-fluoro-2-bromo-1,2-diphenylethylene；α-bromo-α'-fluoro-cis-stilbene；α-Brom-α'-fluor-cis-stilben；α-Brom-α'-fluorstilben；[(Z)-1-bromo-2-fluoro-2-phenylethenyl]benzene
• CAS: 109084-42-6
• 化学式: C₁₄H₁₀BrF
• 分子量: 277.136
• InChiKey: VPPNHEGIONNLHS-YPKPFQOOSA-N

物化性质

• 熔点：
  43-45 °C
• 沸点：
  325.0±42.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-(1-bromo-2-fluoroethene-1,2-diyl)dibenzene 、 4-(2-(哌啶-1-基)乙氧基)苯基硼酸频哪醇酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 苯 为溶剂， 以72%的产率得到1-[2-[4-[(Z)-2-fluoro-1,2-diphenylethenyl]phenoxy]ethyl]piperidine
  参考文献：
  名称：

  Synthesis and growth inhibition activity of fluorinated derivatives of tamoxifen

  摘要：

  The design and synthesis of 11 fluorinated derivatives of tamoxifen are described. Growth inhibition values (GI(50)) on human HT-29, M21, MCF7, and MDA-MB-231 tumor cells are also reported. In general, the GI(50) values are similar or slightly higher than tamoxifen with the most active compound on MCF7 cell line having a GI(50) = 3.6 mu M. Surprisingly, as opposed to tamoxifen, both geometrical isomers behave similarly. We hypothesize that this behavior is due to in vitro isomerization of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.057
• 作为产物：
  描述：

  (1,1-二氟-2-苯基乙基)苯 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙二醇 为溶剂， 生成 (Z)-(1-bromo-2-fluoroethene-1,2-diyl)dibenzene
  参考文献：
  名称：

  Rearrangement Accompanying the Addition of Fluorine to 1,1-Diarylethylenes

  摘要：

  DOI：

  10.1021/ja00894a016

文献信息

• Chemistry of organo halogenic molecules. Part XCIV. The effect of fluorine on photochemical carbon-halogen bond cleavage in Z and E-1-fluoro-2-Halo-1,2-diphenylethylenes.
  作者：A. Gregorčič、M. Zupan

  DOI：10.1016/s0022-1139(00)81541-9

  日期：1988.11

  Introduction of fluorine on the olefinic carbon atom in the β-position to a carbon-halogen bond increased the photocleavage compared to the unsubstituted substrate, and reduced the electron transfer from the caged radical-pair to cationic intermediates. Increased solvent polarity resulted in enhanced photocleavage of the carbon-halogen bond.

  在λ＝ 253.7nm处辐照Z和E-1-氟-2-卤代1,2-二苯基乙烯，得到Z和E-2-氟-1,2-二苯基乙烯和1,2-二苯基乙炔。光转化取决于分子的几何形状，存在的卤素原子和所用的溶剂。与未取代的底物相比，将氟在β位置的烯烃碳原子上引入碳-卤素键会增加光裂解，并减少电子从笼形自由基对向阳离子中间体的转移。溶剂极性的增加导致碳-卤素键的光裂解增强。
• Bornstein; Borden, Chemistry and industry, 1958, p. 441
  作者：Bornstein、Borden

  DOI：——

  日期：——
• Stereocontrolled Approach to Bromofluoroalkenes and Their Use for the Synthesis of Tri- and Tetrasubstituted Fluoroalkenes
  作者：Grégory Landelle、Pier Alexandre Champagne、Xavier Barbeau、Jean-François Paquin

  DOI：10.1021/ol8027412

  日期：2009.2.5

  An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.
• GREGORCIC A.; ZUPAN M., VESTN. SLOVEN. KEM. DRUS., 33,(1986) N 3, 325-338
  作者：GREGORCIC A.、 ZUPAN M.

  DOI：——

  日期：——