(Z)-1-chloro-1,2-difluoro-2-(2-thienyl)ethene | 698-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Z)-1-chloro-1,2-difluoro-2-(2-thienyl)ethene
• 英文别名: 2-(2-chloro-1,2-difluoro-vinyl)-thiophene；2-(2-Chlor-1,2-difluor-vinyl)-thiophen；2-[(Z)-2-chloro-1,2-difluoroethenyl]thiophene
• CAS: 698-05-5
• 化学式: C₆H₃ClF₂S
• 分子量: 180.606
• InChiKey: KNEIFECRFWIDMW-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-chloro-1,2-difluoro-2-(2-thienyl)ethene 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2-(1,2-difluoro-2-chlorovinyl)-5-thienyllithium
  参考文献：
  名称：

  Starostina, T. A.; Rybakova, L. F.; Shifrina, R. R., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 9, p. 1678 - 1681

  摘要：

  DOI：
• 作为产物：
  描述：

  三氟氯乙烯 生成 (Z)-1-chloro-1,2-difluoro-2-(2-thienyl)ethene
  参考文献：
  名称：

  MARTIN, S.;SAUVETRE, R.;NORMANT, J. -F., TETRAHEDRON LETT., 1982, 23, N 42, 4329-4332

  摘要：

  DOI：

文献信息

• Stereospecific synthesis of (E)- and (Z)-1-chloro-1,2-difluorostyrenes
  作者：Chongsoo Lim、Donald J. Burton

  DOI：10.1016/j.jfluchem.2014.07.032

  日期：2014.11

  2-difluoro-1-iodoethene and (E)-2-chloro-1,2-difluoro-1-iodoethene successfully form stable zinc reagents. The zinc reagents successfully undergo Negishi coupling reactions with substituted aryl iodides to form (E)- and (Z)-1-chloro-1,2-difluorostyrenes.

  （Ž）-2-氯-1,2-二氟-1- iodoethene和（Ë）-2-氯-1,2-二氟-1- iodoethene成功形成稳定的锌试剂。锌试剂成功地经历与取代的芳基碘化物Negishi偶联反应形式（ë） -和（Ž）-1-氯-1,2- difluorostyrenes。
• Elimination Reaction of Fluoroölefins with Organolithium Compounds
  作者：STANLEY DIXON

  DOI：10.1021/jo01110a005

  日期：1956.4
• Reaction de perhalostyrenes avec les organolithiens. Preparation d'aryl-1 alcynes-1 ramifies par l'intermediaire d'aryl fluoro acetylenes
  作者：Sophie Martin、Raymond Sauvêtre、Jean-F. Normant

  DOI：10.1016/s0040-4039(00)85592-6

  日期：1982.1
• Synthesis of Conjugated <i>F</i>-Polyenes Containing Thienyl Ring Systems
  作者：Alexander B. Shtarev、Zdeněk Chvátal

  DOI：10.1021/jo962325x

  日期：1997.8.1

  Novel 1-substituted F-1,3-butadienes ThioAr-CF=CFCF=CF2, ThioAr = 2-thienyl and 2-benzo[b]thienyl, and symmetrically 1,4-disubstituted F-1,3-butadienes ThioAr-CF=CFCF=CF-ThioAr, ThioAr = 5-R'-2-thienyl (R' = Me, SiMe3, CF=CFCl), 3-thienyl, and 4-dibenzo[b,d]thienyl, inclusive of the above-named substituents, were prepared by the reaction of organolithium derivatives with F-1,3-butadiene (PFBD). Monothioaryl-substituted F-1,3-butadienes were used as intermediates in subsequent reactions with other (thioaryl)organolithium derivatives for the synthesis of a new series of unsymmetrically substituted alpha,omega-bis(thioaryl)-F-polyenes ThioAr-(CF=CF)(n)-ThioAr', where n = 2, ThioAr, ThioAr' = 4-RC2H4 (R = H, Me, OC6H11, NMe2), 2-thienyl, 5-methyl-2-thienyl, 2-benzo[b]thienyl, 4-dibenzo[b,d]thienyl, and for n = 3, ThioAr = 2-thienyl, ThioAr' = 5-methyl-2-thienyl. The reaction of 2,5-dilithiothiophene with 1-(2-thienyl)-F-1,3-butadiene affords 2,5-bis-[4-(2-thienyl)-1,2,3,4-tetrafluoro-1,3-butadienyl]thiophene (5). 2,5-Thienylene-F-polyenylene polymers were prepared by the reaction of 2,5-dilithio- and 2,5-bis(bromomagnesio)thiophene derivatives with PFBD and F-ethylene. The oligomers 5 and 2,5-bis[2-(2-thienyl)-1,2-difluoroethylenyl]- thiophene (16) were found to possess liquid crystalline properties. The reaction of 1,4-bis(2-thienyl)-F-1,3-butadiene with nitric acid led to substitution in one or in both thienyl rings at position 5. NMR, electronic spectra, and structural aspects of the title compounds are discussed.