1-fluoro-4-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene | 1093645-87-4

• 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-fluoro-4-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene
• CAS: 1093645-87-4
• 化学式: C₂₁H₂₁F
• 分子量: 292.396
• InChiKey: IBZVAFAEKYORCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  氧杂蒽 、 1-fluoro-4-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以92%的产率得到9-(1-(4-fluorophenyl)-4-methyl-1-phenyl-3-(prop-1-en-2-yl)penta-1,3-dien-2-yl)-9H-xanthene
  参考文献：
  名称：

  Reactions of vinylidenecyclopropanes with xanthydrol and xanthene

  摘要：

  Vinylidenecyclopropanes undergo ring-opening reactions with xanthydrol in the presence of BF(3)center dot OEt(2) or with xanthene in the presence of DDQ at 0 degrees C in 1,2-dichloroethane to give the corresponding conjugate triene derivatives in moderate to good yields. Plausible reaction mechanisms have been discussed on the basis of previous literature and the control experiments. The further transformation of these trienes has been disclosed in DCE in the presence of BF(3)center dot OEt(2) along with a plausible reaction mechanism. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.004
• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 1-(2,2-dibromo-1-phenylcyclopropyl)-4-fluorobenzene 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-fluoro-4-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene
  参考文献：
  名称：

  制备多取代环戊烷的催化方法：[3 + 2]偏二酰亚胺催化的亚乙烯基环丙烷与活化烯烃的环加成反应

  摘要：

  [3 + 2]亚乙烯基环丙烷（VDCPs）与缺电子烯烃如甲基乙烯基酮（MVK）和丙烯醛的环加成反应在催化量的三氟甲基酰亚胺（Tf 2 NH）的存在下平稳进行，得到相应的官能团环戊烷的收率高到高。

  DOI：

  10.1021/jo802294s

文献信息

• Triflic imide-catalyzed cascade cycloaddition and Friedel–Crafts reaction of diarylvinylidenecyclopropanes with ethyl 5,5-diarylpenta-2,3,4-trienoate
  作者：Wei Li、Min Shi

  DOI：10.1039/b903965a

  日期：——

  Triflic imide-catalyzed cascade cycloaddition and Friedel–Crafts reaction of diarylvinylidenecyclopropanes with ethyl 5,5-diarylpenta-2,3,4-trienoates provided a variety of novel polycyclic ester derivatives in moderate to good yields under mild conditions.

  三氟甲基亚胺催化的级联环加成和Friedel-Crafts反应，将二芳基乙烯基环丙烷与乙基5,5-二芳基戊-2,3,4-三烯酸酯反应，在温和条件下提供了多种新颖的多环酯衍生物，产率中等至良好。
• BF3⋅OEt2-Catalyzed Intermolecular Reactions of Vinylidenecyclopropanes with Bis(p-alkoxyphenyl)methanols: A Novel Cationic 1,4-Aryl-Migration Process
  作者：Lei Wu、Min Shi、Yuxue Li

  DOI：10.1002/chem.200903131

  日期：——

  BF3⋅OEt2‐catalyzed reactions of vinylidenecyclopropanes (VDCPs) 1 with bis(aryl)methanols 2 were thoroughly investigated. When VDCPs 1 reacted with electron‐rich bis(aryl)methanols 2, diastereomeric rotamers of indene derivatives formed in excellent yields by a novel cationic 1,4‐aryl migration between two carbon atoms and the subsequent intramolecular Friedel–Crafts reaction pathways in the presence

  BF 3 ⋅OEt 2层的vinylidenecyclopropanes（VDCPs） -催化的反应1与双（芳基）基甲醇2进行了彻底调查。当VDCPs 1与富电子的双（芳基）甲醇2反应时，茚衍生物的非对映异构体以优异的收率形成，这是由于存在两个碳原子之间的新型阳离子1,4-芳基迁移以及随后的分子内Friedel-Crafts反应路径的BF 3 ⋅OEt 2温和的条件下。至于缺电子或少电子的双（芳基）甲醇2要么通过直接去质子化以高收率形成三烯产物，要么通过直接分子内Friedel-Crafts反应产生另一种类型的茚衍生物，这取决于VDCPs的环丙烷上的取代基。另外，进行了DFT计算以解释实验结果。根据实验和计算结果，提出了所有这些转换的合理机制。
• Addition of diphenylphosphinodithioic acid and thioacetic acid with vinylidenecyclopropanes: reversed regioselectivities
  作者：Wei Li、Min Shi

  DOI：10.1016/j.tet.2009.06.090

  日期：2009.8

  The reaction of vinylidenecyclopropanes 1 with diphenylphosphinodithioic acid produces the adducts 3 in good to high yields in toluene upon heating at 100 °C within 1 h, whereas adducts 5 are obtained in excellent yields in reversed regioselectivity from the reaction of 1 with thioacetic acid under identical conditions. The radical reaction processes have been discussed on the basis of deuterium labeling

  亚乙烯基环丙烷1与二苯基次膦二硫代酸的反应在100°C下加热1小时后，在甲苯中生成高至高收率的加合物3，而在相同条件下1与硫代乙酸的反应则以极高的收率获得了高收率的加合物5。情况。在氘标记实验和在自由基抑制剂（TEMPO和BHT）或质子清除剂（DTBMP）存在下的对照实验的基础上，对自由基反应过程进行了讨论。
• Palladium-Catalyzed Coupling Reactions of Diarylvinylidenecyclopropanes with 2-Iodophenol and<i>N</i>-(2-Iodophenyl)-4-methylbenzenesulfonamide
  作者：Wei Li、Min Shi

  DOI：10.1002/ejoc.200800955

  日期：2009.1

  A palladium-catalyzed cross-coupling reaction of diarylvinylidenecyclopropanes with 2-iodophenol and N-(2-iodophenyl)-4-methylbenzenesulfonamide provided a variety of cyclopropane-containing 2,2-diaryl-3-tetramethylcyclopropylidene-2,3-dihydrobenzofuran and 2,2-diaryl-3-tetramethylcyclopropylidene-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole derivatives in moderate-to-good yields.(© Wiley-VCH Verlag

  钯催化的二芳基亚乙烯基环丙烷与 2-碘苯酚和 N-(2-碘苯基)-4-甲基苯磺酰胺的交叉偶联反应提供了多种含环丙烷的 2,2-二芳基-3-四甲基环丙烷-2,3-二氢苯并呋喃和 2 ,2-二芳基-3-四甲基环亚丙基-1-(甲苯-4-磺酰基)-2,3-二氢-1H-吲哚衍生物，产率中等。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451德国魏因海姆，2009）
• Reactions of vinylidenecyclopropanes with xanthydrol and xanthene
  作者：Wei Yuan、Min Shi

  DOI：10.1016/j.tet.2010.07.004

  日期：2010.8

  Vinylidenecyclopropanes undergo ring-opening reactions with xanthydrol in the presence of BF(3)center dot OEt(2) or with xanthene in the presence of DDQ at 0 degrees C in 1,2-dichloroethane to give the corresponding conjugate triene derivatives in moderate to good yields. Plausible reaction mechanisms have been discussed on the basis of previous literature and the control experiments. The further transformation of these trienes has been disclosed in DCE in the presence of BF(3)center dot OEt(2) along with a plausible reaction mechanism. (C) 2010 Elsevier Ltd. All rights reserved.