| 1589050-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1589050-83-8
• 化学式: C₈H₅F₂I
• 分子量: 266.029
• InChiKey: VGDMTDOOBXBYIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  在 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 以82 %的产率得到1-iodo-3-(1,2,2,2-tetrafluoroethyl)benzene
  参考文献：
  名称：

  Streamlined Electrochemical Dihalogenation (F, Cl, and Br) of gem‐Difluoroalkenes Using Hydrogen Halides as Reagents

  摘要：

  We established a straightforward electrochemical dihalogenation (F, Cl, and Br) process for gem‐difluoroalkenes. This reaction exhibits a broad functional group tolerance and has been effectively utilized in the construction of complex molecules. The subsequent synthetic transformations of the products have highlighted the adaptable nature of the dihalogenated compounds, demonstrating their potential application in drug discovery and the investigation of innovative materials. The effective utilization of the dihalogenated product for 18F‐labeling represents a novel approach in generating highly potent 18F‐labeled tracers.

  DOI：

  10.1002/ejoc.202400351
• 作为产物：
  描述：

  3-碘苯甲醛 、 sodium chlorodifluoroacetate 在 N-甲基吡咯烷酮 、 三苯基膦 作用下， 生成
  参考文献：
  名称：

  偕二氟烯烃与醛和酮的电催化脱氟交叉偶联

  摘要：

  描述了偕二氟烯烃与羰基化合物的电化学脱氟交叉偶联，合成了高度立体选择性的单氟烯烃烯丙醇。该反应可耐受多种官能团，并已成功应用于合成复杂分子。机理研究表明，该反应从偕二氟烯烃的电子还原开始，生成自由基负离子，再经过β-氟化物消除，随后还原形成阴离子。这些阴离子随后被羰基化合物捕获以提供目标产物。

  DOI：

  10.1021/acs.orglett.3c03788

文献信息

• Sterically Controlled Cu-Catalyzed or Transition-Metal-Free Cross-Coupling of <i>gem</i>-Difluoroalkenes with Tertiary, Secondary, and Primary Alkyl Grignard Reagents
  作者：Wenpeng Dai、Hongyan Shi、Xianghu Zhao、Song Cao

  DOI：10.1021/acs.orglett.6b02026

  日期：2016.9.2

  transition-metal-free cross-coupling of gem-difluoroalkenes with tertiary, secondary, and primary alkyl Grignard reagents has been developed. Remarkably, the tertiary and secondary alkylation of gem-difluoroalkenes proceeded very smoothly in the presence of 25 mol % of CuCN or under transition-metal-free conditions, affording the tertiary and secondary alkyl-substituted fluoroalkenes in good to excellent yields with

  已经开发出一种健壮的铜催化或无过渡金属的宝石-二氟烯烃与叔，仲和伯烷基格氏试剂的交叉偶联。值得注意的是，在25 mol％的CuCN存在下或在无过渡金属的条件下，宝石-二氟烯烃的叔和仲烷基化反应进行得非常顺利，从而以良好的收率和优异的Z立体选择性提供了叔或仲烷基取代的氟代烯烃。 。
• Copper-Catalyzed Coupling Cyclization of <i>gem</i>-Difluoroalkenes with Activated Methylene Carbonyl Compounds: Facile Domino Access to Polysubstituted Furans
  作者：Xuxue Zhang、Wenpeng Dai、Wei Wu、Song Cao

  DOI：10.1021/acs.orglett.5b01123

  日期：2015.6.5

  A novel and efficient CuI-catalyzed synthesis of 2,3,5-trisubstituted furans was developed via coupling cyclization of gem-difluoroalkenes with active methylene carbonyl compounds such as 1,3-dicarbonyl compounds, acetoacetonitrile, and phenylsulfonylacetone with the assistance of a base. Commercial availability of substrates or reagents, good to high isolated yields, and excellent functional group

  通过宝石-二氟烯烃与活性亚甲基羰基化合物（例如1,3-二羰基化合物，乙酰乙腈和苯磺酰丙酮）的偶联环化，开发了新颖，高效的CuI催化的2,3,5-三取代呋喃合成方法。底物或试剂的商业可得性，良好或较高的分离产率以及出色的官能团相容性，使这种转化成为合成各种呋喃的有力工具。提出了一种可能的机制，涉及到烯丙基酮。
• Cu-Catalyzed Stereoselective Borylation of <i>gem</i>-Difluoroalkenes with B₂pin₂
  作者：Juan Zhang、Wenpeng Dai、Qingyun Liu、Song Cao

  DOI：10.1021/acs.orglett.7b01430

  日期：2017.6.16

  A novel and efficient method for the synthesis of (Z)-fluorinated alkenylboronic acid pinacol esters via Cu-catalyzed stereoselective borylation of gem-difluoroalkenes using bis(pinacolato)diboron (B2pin2) as the boron source with the assistance of NaOtBu and Xantphos at room temperature was developed.

  一种新的高效方法，以双（频哪醇）二硼烷（B 2 pin 2）为硼源，在NaO t的辅助下，通过Cu催化的宝石-二氟烯烃立体选择性硼化来合成（Z）氟代烯基硼酸频哪醇酯。开发了室温下的Bu和Xantphos。
• Synthesis of N,N-disubstituted 2-aminothiophenes by the cyclization of gem-difluoroalkenes with β-keto thioamides
  作者：Xuxue Zhang、Mingsheng Wu、Juan Zhang、Song Cao

  DOI：10.1039/c7ob00368d

  日期：——

  gem-difluoroalkenes with β-keto tertiary thioamides is described. The reactions proceed smoothly with the assistance of K2CO3 under transition-metal-free conditions, affording a variety of valuable N,N-disubstituted 2-aminothiophenes in moderate to good yields.

  描述了一种新的有效的方法，该方法可通过用β-酮基叔硫酰胺环合宝石-二氟烯烃来构建高度官能化的氨基噻吩。在无过渡金属的条件下，反应在K 2 CO 3的帮助下顺利进行，以中等至良好的收率提供了各种有价值的N，N-二取代的2-氨基噻吩。
• Synthesis of <i>N</i>-(α-Fluorovinyl)azoles by the Reaction of Difluoroalkenes with Azoles
  作者：Yang Xiong、Xuxue Zhang、Tao Huang、Song Cao

  DOI：10.1021/jo5005845

  日期：2014.7.18

  A mild and versatile method for the construction of C-N bonds by the reaction of (2,2-difluorovinyl)arenes with various N-H-containing heterocycles in the presence of K3PO4 has been developed. The reaction proceeded efficiently at room temperature (25 degrees C) affording the (E)-N-alpha-fluorovinyl derivatives of azoles 3 in good to excellent yields with relatively high stereoselectivity.