(Z)-1,2-dibromo-3-(4-fluorophenyl)-2-propene | 1600528-39-9

• 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)-1,2-dibromo-3-(4-fluorophenyl)-2-propene
• 英文别名: 1-[(Z)-2,3-dibromoprop-1-enyl]-4-fluorobenzene
• CAS: 1600528-39-9
• 化学式: C₉H₇Br₂F
• 分子量: 293.961
• InChiKey: ILKQZCIXDVJFIB-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  (Z)-1,2-dibromo-3-(4-fluorophenyl)-2-propene 、 邻苯二酚 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以63%的产率得到(Z)-2-(4-fluorobenzylidene)-2,3-dihydrobenzo[b][1,4]dioxine
  参考文献：
  名称：

  （Z）-1,2-二溴-3-芳基-2-丙烯与（Z）-2-亚芳基-2,3-二氢苯并[ b ] [1,4]二恶英的无过渡金属非对映异构合成儿茶酚

  摘要：

  在140°C下以Cs 2 CO 3为碱在取代的（Z）-1,2-二溴-3-苯基-2-丙烯与取代的邻苯二酚之间进行的无过渡金属非对映异构反应可产生仅被取代的（Z）-2-亚芳基-2,3-二氢苯并[ b ] [1,4]二恶英的产率高达89％。实验以及量子化学计算均支持以下假设：一锅转化以分子间O-烯丙基化/分子内O-乙烯基化的方式进行。

  DOI：

  10.1016/j.tet.2020.131482
• 作为产物：
  描述：

  对氟肉桂醛 在 吡啶 、 sodium tetrahydroborate 、 溴 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 (Z)-1,2-dibromo-3-(4-fluorophenyl)-2-propene
  参考文献：
  名称：

  2,3-Dihalo-1-propenes as Building Blocks in Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans

  摘要：

  The Cu(I)-catalyzed reaction of 2,3-dibromo-1-propenes with beta-ketoesters and 1,3-diketones, respectively, in DMF at 120 degrees C using Cs2CO3 as a base and hydroquinone as an additive exclusively delivers 2,3,5-trisubstituted furans and related compounds with yields up to 96%. The highly regioselective domino process is based on an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.

  DOI：

  10.1021/ol502371j

文献信息

• Selectfluor-mediated mild oxidative halogenation and thiocyanation of 1-aryl-allenes with TMSX (X=Cl, Br, I, NCS) and NH4SCN
  作者：Kenneth K. Laali、Ganesh C. Nandi、Scott D. Bunge

  DOI：10.1016/j.tetlet.2014.02.110

  日期：2014.4

  Presence of TMSX (X = Cl, Br, I) unleashes the oxidative character of Selectfluor and provides a mild dihalogenation method for 1-arylallenes. Preference for 2,3-addition was observed with TMSCl in MeCN irrespective of the nature of the substituent on the aryl moiety, whereas 1,2-addition was preferred in [BMIM][BF4]. With TMSBr and TMSI only products corresponding to 2,3-addition were observed. Reactions carried out with TMSBr in IL solvents gave the corresponding monobromoalkenes as a major product along with the isomeric dibromo-alkenes. Reaction with NH4SCN provided convenient access to dithiocyanate derivatives. The same products were formed via TMS-NCS/Selectfluor. Formation of common products via TMSNCS and NH4SCN points to the formation and interplay of SCN+/NCS+ as incipient electrophiles. (C) 2014 Elsevier Ltd. All rights reserved.
• 2,3-Dihalo-1-propenes as Building Blocks in Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans
  作者：Dietmar Schmidt、Chandi C. Malakar、Uwe Beifuss

  DOI：10.1021/ol502371j

  日期：2014.9.19

  The Cu(I)-catalyzed reaction of 2,3-dibromo-1-propenes with beta-ketoesters and 1,3-diketones, respectively, in DMF at 120 degrees C using Cs2CO3 as a base and hydroquinone as an additive exclusively delivers 2,3,5-trisubstituted furans and related compounds with yields up to 96%. The highly regioselective domino process is based on an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.
• Transition metal-free diastereospecific synthesis of (Z)-2-arylidene-2,3-dihydrobenzo[b][1,4]dioxines by reaction of (Z)-1,2-dibromo-3-aryl-2-propenes with catechols
  作者：Szymon P. Rekowski、Aabid A. Wani、Jürgen Conrad、Prasad V. Bharatam、Wolfgang Frey、Uwe Beifuss

  DOI：10.1016/j.tet.2020.131482

  日期：2020.10

  A transition metal-free, diastereospecific reaction between substituted (Z)-1,2-dibromo-3-phenyl-2-propenes and substituted catechols using Cs2CO3 as a base at 140 °C for 18 h delivers exclusively substituted (Z)-2-arylidene-2,3-dihydrobenzo[b][1,4]dioxines in yields up to 89%. Experiments as well as quantum chemical calculations support the assumption that the one pot transformation proceeds as an

  在140°C下以Cs 2 CO 3为碱在取代的（Z）-1,2-二溴-3-苯基-2-丙烯与取代的邻苯二酚之间进行的无过渡金属非对映异构反应可产生仅被取代的（Z）-2-亚芳基-2,3-二氢苯并[ b ] [1,4]二恶英的产率高达89％。实验以及量子化学计算均支持以下假设：一锅转化以分子间O-烯丙基化/分子内O-乙烯基化的方式进行。