1-fluoro-1-iodo-4-phenyl-1-butene | 154092-22-5

• 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-1-iodo-4-phenyl-1-butene
• 英文别名: [(E)-4-fluoro-4-iodobut-3-enyl]benzene
• CAS: 154092-22-5
• 化学式: C₁₀H₁₀FI
• 分子量: 276.092
• InChiKey: MDOBXKQYNQJBLH-CSKARUKUSA-N

物化性质

• 沸点：
  271.6±35.0 °C(Predicted)
• 密度：
  1.596±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-fluoro-1-iodo-4-phenyl-1-butene 、 (2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 12.0h， 以89%的产率得到4-fluoro-1-phenyl-6-[2-(1,3-dioxolanyl)]-3(Z)-hexene
  参考文献：
  名称：

  Synthesis of the Multisubstituted Halogenated Olefins via Cross-Coupling of Dihaloalkenes with Alkylzinc Bromides

  摘要：

  The 1-fluoro-1-haloalkenes undergo Pd-catalyzed Negishi cross-couplings with primary alkylzinc bromides to give multisubstituted fluoroalkenes. The alkylation was trans-selective giving pure Z-fluoroalkenes in most cases. The highest yields were obtained with Pd-2(dba)(3) and PdCl2(dppb) catalysts but the best stereochemical outcome was obtained with less reactive Pd(PPh3)(4). The tertiary alkylzincs also produced desired fluoroalkenes in high yields. Coupling of beta,beta-dichloro styrene with organozinc reagent resulted in the formation of monocoupled product.

  DOI：

  10.1021/jo051980e
• 作为产物：
  描述：

  (E)-2-(phenylethyl)-1-(tributylstannyl)-1-fluoroethene 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到1-fluoro-1-iodo-4-phenyl-1-butene
  参考文献：
  名称：

  Synthesis of the Multisubstituted Halogenated Olefins via Cross-Coupling of Dihaloalkenes with Alkylzinc Bromides

  摘要：

  The 1-fluoro-1-haloalkenes undergo Pd-catalyzed Negishi cross-couplings with primary alkylzinc bromides to give multisubstituted fluoroalkenes. The alkylation was trans-selective giving pure Z-fluoroalkenes in most cases. The highest yields were obtained with Pd-2(dba)(3) and PdCl2(dppb) catalysts but the best stereochemical outcome was obtained with less reactive Pd(PPh3)(4). The tertiary alkylzincs also produced desired fluoroalkenes in high yields. Coupling of beta,beta-dichloro styrene with organozinc reagent resulted in the formation of monocoupled product.

  DOI：

  10.1021/jo051980e

文献信息

• A Stereoselective method to (E)- and (Z)-fluorovinyl phosphonates Utilizing Palladium(0) coupling methodology
  作者：Raymond S. Gross、Shujaath Mehdi、James R. McCarthy

  DOI：10.1016/s0040-4039(00)79286-0

  日期：1993.11

  The first stereoselective method to both (E)- and (Z)-fluorovinyl phosphonates from fluorovinyl iodides was developed utilizing a palladium(0) based coupling protocol. This method allowed the preparation of (E)- and (Z)-fluorovinyl phosphonic acid analogs of glucose-6-phosphate that were designed to be mechanism-based inhibitors of inositol synthase.