1-bromo-1-fluoro-2-(3-nitrophenyl)-ethene | 459132-90-2

• 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: 1-bromo-1-fluoro-2-(3-nitrophenyl)-ethene
• 英文别名: 1-(2-bromo-2-fluoroethenyl)-3-nitrobenzene
• CAS: 459132-90-2
• 化学式: C₈H₅BrFNO₂
• 分子量: 246.036
• InChiKey: USDFQQJBLXMYBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-bromo-1-fluoro-2-(3-nitrophenyl)-ethene 在 四(三苯基膦)钯 六正丁基二锡 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 131.0h， 以0.11 g的产率得到(1Z,3Z)-2,3-difluoro-1,4-di(3-nitrophenyl)-butadiene
  参考文献：
  名称：

  Stereospecific preparation of symmetrical (1Z, 3Z)- and (1E, 3E)-2,3-difluoro-1,4-disubstituted-buta-1,3-dienes from 1-bromo-1-fluoroalkenes

  摘要：

  A straightforward method to prepare symmetrical (1Z, 3Z)- and (1E, 3E)-2,3-difluoro-1,4-disubstituted-buta-1,3-dienes is described. High E/Z ratio 1-bromo-l-fluoroalkenes, prepared by isomerization from the E/Z approximate to 1:1 isomeric mixtures, reacted with Bu3SnSnBu3 and Pd(PPh3)(4) to afford (1Z, 3Z)-2,3-difluoro-1,4-disubstituted-buta-1,3-dienes in good yield. (Z)-1-Bromo-1-fluoroalkenes, which were prepared by kinetic reduction from 1-bromo-1-fluoroalkenes (E/Z approximate to 1:1), can undergo similar reaction with Bu3SnSnBu3 and Pd(PPh3)(4)/Cul to prepare (lE, 3E)-2,3difluoro-1,4-disubstituted-buta-1,3-dienes. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.10.002
• 作为产物：
  描述：

  氟三溴甲烷 、 间硝基苯甲醛 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以53%的产率得到1-bromo-1-fluoro-2-(3-nitrophenyl)-ethene
  参考文献：
  名称：

  通过高E / Z比与（Z）-1-溴-1-氟烯烃的钯催化交叉偶联反应立体选择性地制备（E）-和（Z）-α-氟代苯甲酸酯

  摘要：

  描述了制备（E）-和（Z）-α-氟丁苯醚的高度立体选择性的方法。1-溴-1-氟烯烃（É / ž ≈1：1），可容易获得的起始原料，异构化成高é / Ž由存储在-20℃下或通过在254nm下光解比率。这些高E / Z 1-溴-1-氟烯烃与芳基锡烷之间的斯蒂勒偶联以高立体选择性产生（Z）-α-氟代苯乙烯。（Z）-1-溴-1-氟烯烃，从动力学上与1-溴-1-氟烯烃分离（E / Z≈1：1），可参与Suzuki偶联反应以立体选择性地产生（E）-α-氟代苯乙烯。

  DOI：

  10.1021/jo060068i

文献信息

• Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes
  作者：Laëtitia Chausset-Boissarie、Nicolas Cheval、Christian Rolando

  DOI：10.3390/molecules25235532

  日期：——

  versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with

  单氟烯烃是有机合成、药物化学和材料科学中的多功能氟化合成子。鉴于烷基取代的单氟烯烃的重要性，这些部分的有效合成仍然是合成挑战。在此，我们描述了一种温和而有效的方法，通过在温和条件下通过立体有择钯催化的溴氟烯烃与伯和应变仲烷基硼酸的烷基化来获得单氟烯烃。这种新颖的策略可以高产率地获得各种功能化的三取代和四取代的单氟烯烃，具有良好的官能团耐受性，独立于嵴溴氟烯烃的几何形状。
• Diels-Alder Reaction of β-Fluoro-β-nitrostyrenes. Synthesis of Mono-fluorinated Six-Membered Derivatives
  作者：Roman V. Larkovich、Savva A. Ponomarev、Alexander S. Aldoshin、Andrey A. Tabolin、Sema L. Ioffe、Valentine G. Nenajdenko

  DOI：10.1002/ejoc.202000054

  日期：2020.5.10

  TOC Text: The Diels‐Alder reaction of β‐fluoro‐β nitrostyrenes with some linear dienes is reported. The kinetic studies were carried out to reveal substituent effect and activation parameters of the reaction. A new family of monofluorinated cyclohexenes 2 was prepared. The further transformation of 2 into biphenyls 3 based on base‐induced elimination of HNO2 followed by oxidative aromatization were

  TOC文本：报告了β-氟-β硝基苯乙烯与某些线性二烯的Diels-Alder反应。进行动力学研究以揭示取代基效应和反应的活化参数。制备了一个新的单氟环己酮家族2。描述了基于碱诱导的HNO 2消除和氧化芳构化作用，将2进一步转化为联苯3。
• Stereospecific preparation of (Z)-α-fluorostilbenes via a kinetically controlled palladium-catalyzed cross-coupling reaction of high E/Z ratio 1-bromo-1-fluorostyrenes and aryl stannanes
  作者：Jianjun Xu、Donald J Burton

  DOI：10.1016/s0040-4039(02)00357-x

  日期：2002.4

  for 1-bromo-1-fluorostyrenes by isomerization from the original E/Z ratios of approximately 1:1. The palladium-catalyzed cross-coupling reaction of high E/Z ratio 1-bromo-1-fluorostyrenes with aryl stannanes gives (Z)-α-fluorostilbenes stereospecifically in good yields.

  通过异构化从大约1：1的原始E / Z比率获得1-溴-1-氟苯乙烯的高E / Z比率。高E / Z比的1-溴-1-氟苯乙烯与芳基锡烷的钯催化交叉偶联反应可立体立体地获得高收率的（Z）-α-氟代苯乙烯。
• Highly Stereoselective Synthesis of (<i>E</i>)- and (<i>Z</i>)-α-Fluoro-α,β-unsaturated Esters and (<i>E</i>)- and (<i>Z</i>)-α-Fluoro-α,β-unsaturated Amides from 1-Bromo-1-fluoroalkenes via Palladium-Catalyzed Carbonylation Reactions
  作者：Jianjun Xu、Donald J. Burton

  DOI：10.1021/jo050314a

  日期：2005.5.1

  (Z)-1-bromo-1-fluoroalkenes and the reduced products underwent similar palladium-catalyzed carboalkoxylation reactions at 70 °C, and the (E)-α-fluoro-α,β-unsaturated esters were stereospecifically obtained. This methodology was also successfully applied for the stereospecific synthesis of (Z)- and (E)-α-fluoro-α,β-unsaturated amides: the palladium-catalyzed carboamidation reaction of high E/Z and (Z)-1-bromo-1-fluoroalkenes

  描述了（E）-和（Z）-α-氟-α，β-不饱和酯和（E）-和（Z）-α-氟-α，β-不饱和酰胺的高度立体选择性合成。1-溴-1-氟烯烃（É / ž ≈1:1），它们是容易获得的原料，已经发现异构化为高È / ž比在-20℃下贮存1周后的或通过在254光解纳米 由于已发现（E）异构体在室温下在Pd（0）催化的反应中比相应的（Z）异构体反应更快，因此钯催化的高E / Z的碳烷氧基化反应1-溴-1-氟烯烃导致高ž / é（ż / é ≥98：2）的α氟α，β -不饱和酯的比率。当1-溴-1-氟烯烃（É / ž ≈1:1）用HCOOH / NBU反应3 /钯（II）/ DMF中，（ë） -异构体选择性地减小，并且剩余的（Ž）-1-以基本上纯的异构体形式回收了β-溴-1-氟烯烃。将所得的混合物（ż）-1-溴-1-氟烯烃和还原产物进行类似的钯催化反应carboalkoxylation在70℃，和（Ë立
• Stereospecific preparation of (2E, 4Z)-monofluorodienyl esters by the Heck reaction of high E/Z ratio 1-bromo-1-fluorostyrenes
  作者：Jianjun Xu、Donald J Burton

  DOI：10.1016/j.jfluchem.2003.12.005

  日期：2004.5

  High E/Z ratio (E/Z > 75:25) 1-bromo-1-fluorostyrenes, which were prepared by isomerization of 1-bromo-1-fluorostyrenes (E/Z 1:1), underwent the Heck reaction with methyl acrylate, and (2E, 4Z)-methyl 5-aryl-4-fluoropenta-2,4-dienoates were successfully isolated. Heck reactions of (Z)-1-bromo-1-fluorostyrenes also occur. However, the products are difficult to separate in a pure form, since they have an obvious tendency to isomerize on a silica gel column. (C) 2003 Elsevier B.V. All rights reserved.