[3,5-bis(trifluoromethyl)phenyl] N,N-dimethylsulfamate | 1416330-86-3

• 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: [3,5-bis(trifluoromethyl)phenyl] N,N-dimethylsulfamate
• CAS: 1416330-86-3
• 化学式: C₁₀H₉F₆NO₃S
• 分子量: 337.243
• InChiKey: PXCOHAJLHCSCOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [3,5-bis(trifluoromethyl)phenyl] N,N-dimethylsulfamate 、 正丁基氯化镁 在 iron(III) fluoride trihydrate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.0h， 以50%的产率得到1-butyl-3,5-bis(trifluoromethyl)benzene
  参考文献：
  名称：

  Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Sulfamates and Tosylates

  摘要：

  The iron-catalyzed cross-coupling of aryl sulfamates and tosylates has been achieved with primary and secondary alkyl Grignards. This study of iron-catalyzed cross-coupling reactions also examines the isomerization and beta-hydride elimination problems that are associated with the use of isopropyl nucleophiles. While a variety of iron sources were competent in the reaction, the use of FeF3 center dot 3H(2)O was critical to minimize nucleophile isomerization.

  DOI：

  10.1021/ol303130j
• 作为产物：
  描述：

  3,5-二三氟甲基苯酚 、 二甲胺基磺酰氯 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 mineral oil 为溶剂， 以73%的产率得到[3,5-bis(trifluoromethyl)phenyl] N,N-dimethylsulfamate
  参考文献：
  名称：

  Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Sulfamates and Tosylates

  摘要：

  The iron-catalyzed cross-coupling of aryl sulfamates and tosylates has been achieved with primary and secondary alkyl Grignards. This study of iron-catalyzed cross-coupling reactions also examines the isomerization and beta-hydride elimination problems that are associated with the use of isopropyl nucleophiles. While a variety of iron sources were competent in the reaction, the use of FeF3 center dot 3H(2)O was critical to minimize nucleophile isomerization.

  DOI：

  10.1021/ol303130j

文献信息

• Iron-Catalyzed Coupling of Aryl Sulfamates and Aryl/Vinyl Tosylates with Aryl Grignards
  作者：Toolika Agrawal、Silas P. Cook

  DOI：10.1021/ol5024344

  日期：2014.10.3

  The iron-catalyzed coupling of aryl sulfamates and tosylates with aryl Grignard reagents is reported for the first time. The methodology employs air-stable, low-cost FeF3 center dot 3H(2)O and the N-heterocyclic carbene ligand IPr center dot HCl as the preligand to form a long-lived catalyst upon treatment with aryl Grignards. The reaction provides a range of cross-coupled products in good-to-excellent yields. In contrast to previous reports with aryl chlorides, these reactions proceed with low levels of Grignard homocoupling regardless of the iron source.
• Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Sulfamates and Tosylates
  作者：Toolika Agrawal、Silas P. Cook

  DOI：10.1021/ol303130j

  日期：2013.1.4

  The iron-catalyzed cross-coupling of aryl sulfamates and tosylates has been achieved with primary and secondary alkyl Grignards. This study of iron-catalyzed cross-coupling reactions also examines the isomerization and beta-hydride elimination problems that are associated with the use of isopropyl nucleophiles. While a variety of iron sources were competent in the reaction, the use of FeF3 center dot 3H(2)O was critical to minimize nucleophile isomerization.

表征谱图