1-fluoro-3-benzyloxy-1-(phenylsulfonyl)-1-propene

• 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-3-benzyloxy-1-(phenylsulfonyl)-1-propene
• 英文别名: [(E)-3-(benzenesulfonyl)-3-fluoroprop-2-enoxy]methylbenzene
• 化学式: C₁₆H₁₅FO₃S
• 分子量: 306.358
• InChiKey: AXQBRWXDCMYXFD-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二乙基(苯基硫代甲基)磷酸酯 在 Oxone 、 Selectfluor 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 1-fluoro-3-benzyloxy-1-(phenylsulfonyl)-1-propene
  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

• Synthesis of the Multisubstituted Halogenated Olefins via Cross-Coupling of Dihaloalkenes with Alkylzinc Bromides
  作者：Daniela Andrei、Stanislaw F. Wnuk

  DOI：10.1021/jo051980e

  日期：2006.1.1

  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.