(Z)-1,4-diphenyl-1-fluoro-1-butene | 140137-77-5

• 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: (Z)-1,4-diphenyl-1-fluoro-1-butene
• 英文别名: (Z)-1-Fluoro-1,4-diphenylbutene；(Z)-1,4-Diphenyl-1-fluorobutene；[(Z)-1-fluoro-4-phenylbut-1-enyl]benzene
• CAS: 140137-77-5
• 化学式: C₁₆H₁₅F
• 分子量: 226.294
• InChiKey: MMSKTIBIMUSAHY-SSZFMOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-fluoro-4-phenyl-1-[tris(trimethylsilyl)germyl]-1-butene 、 碘苯 在 四(三苯基膦)钯 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以75%的产率得到(Z)-1,4-diphenyl-1-fluoro-1-butene
  参考文献：
  名称：

  Pd-catalyzed couplings of (α-fluoro)vinyl tris(trimethylsilyl)germanes

  摘要：

  The (alpha-fluoro)vinyl tris(trimethylsilyl)germanes undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides upon oxidative treatment with hydrogen peroxide under basic aqueous conditions to give access to fluoroalkenes and fluorodienes with retention of stereochemistry. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.023

文献信息

• New methods for the synthesis of fluoroolefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes and organostannanes
  作者：Chen Chen、Keith Wilcoxen、Charles Q Huang、Nathalie Strack、James R McCarthy

  DOI：10.1016/s0022-1139(99)00172-4

  日期：2000.2

  The palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes and organostannanes provide two new facile methods to 1-substituted 1-fluoroolefins. The reactions proceed with retention of configuration in good to excellent yields.

  1-氟乙烯基卤化物与有机硼烷和有机锡的钯催化的交叉偶联反应为1-取代的1-氟烯烃提供了两种新的简便方法。反应以良好至优异的产率保持构型进行。
• Nucleophilic Desulfinylation of α-Fluoro-β-(alkoxy and silyloxy) Sulfoxides.Effects of the β-Oxy Substituents on Protonation, 1,2-Hydrogen Migration, and Nucleophile Addition to the Fluorocarbenoid Centers
  作者：Hidemitsu Uno、Katsuji Sakamoto、Hitomi Suzuki

  DOI：10.1246/bcsj.65.218

  日期：1992.1

  resulted in the formation of a fluorostilbene derivative, a fluoro enol silyl ether and small amounts of 4-(fluoroacetyl)biphenyl, while a similar reaction of 2-methoxymethoxy analog mainly led to the fluorostilbene derivatives and a simple desulfinylation product. In contrast, both sulfoxides reacted with PhLi to give chlorofluoro compounds and fluoro enol ethers. In these reactions, the stability

  用 PhMgBr 处理 2-（4-联苯基）-2-叔丁基二甲基甲硅烷氧基-1-氯-1-氟乙基苯基亚砜导致形成氟二苯乙烯衍生物、氟烯醇甲硅烷基醚和少量 4-（氟乙酰基）联苯，而 2-甲氧基甲氧基类似物的类似反应主要导致氟二苯乙烯衍生物和简单的脱亚磺酰化产物。相比之下，两种亚砜都与 PhLi 反应生成氯氟化合物和氟烯醇醚。在这些反应中，亚砜部分的亲核去除衍生的类卡宾的稳定性受β-取代基的影响很大，从而控制了产物分布。
• Pd-catalyzed couplings of (α-fluoro)vinyl tris(trimethylsilyl)germanes
  作者：Zhizhong Wang、Aurelio Gonzalez、Stanislaw F. Wnuk

  DOI：10.1016/j.tetlet.2005.06.023

  日期：2005.8

  The (alpha-fluoro)vinyl tris(trimethylsilyl)germanes undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides upon oxidative treatment with hydrogen peroxide under basic aqueous conditions to give access to fluoroalkenes and fluorodienes with retention of stereochemistry. (c) 2005 Elsevier Ltd. All rights reserved.