1,3-二氟-4-硝基-2-(三甲基硅烷)苯 | 186315-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二氟-4-硝基-2-(三甲基硅烷)苯
• 英文名称: 1,3-difluoro-4-nitro-2-(trimethylsilyl)benzene
• 英文别名: 2,6-Difluoro-3-nitrophenyltrimethylsilane；2,4-difluoro-3-(trimethylsilyl)nitrobenzene；(2,6-Difluoro-3-nitrophenyl)(trimethyl)silane；(2,6-difluoro-3-nitrophenyl)-trimethylsilane
• CAS: 186315-85-5
• 化学式: C₉H₁₁F₂NO₂Si
• mdl: MFCD01318141
• 分子量: 231.274
• InChiKey: XMEDCOZETUWHIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险类别码：
  R36/38
• 安全说明：
  S26,S36

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 2,4-二氟硝基苯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以36%的产率得到1,3-二氟-4-硝基-2-(三甲基硅烷)苯
  参考文献：
  名称：

  Metalation of Nitroaromatics with in Situ Electrophiles

  摘要：

  DOI：

  10.1021/jo961839t

文献信息

• Deprotonative Silylation of Aromatic C–H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
  作者：Kanako Nozawa-Kumada、Sayuri Osawa、Midori Sasaki、Isabelle Chataigner、Masanori Shigeno、Yoshinori Kondo

  DOI：10.1021/acs.joc.7b01525

  日期：2017.9.15

  method for the deprotonative silylation of aromatic C–H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert–Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied

  已经开发了一种使用三氟甲基三甲基硅烷（CF 3 SiMe 3，Ruppert-Prakash试剂）和催化量氟化物的芳香族C-H键去质子化甲硅烷基化的方法。在该反应中，认为CF 3 SiMe 3用作碱和亲电子硅。该过程高度耐受杂芳烃和苯上的各种官能团。此外，该方法可以应用于TAC-101的含三甲基甲硅烷基的类似物的合成，TAC-101是对视黄酸受体α（RAR-α）结合具有选择性亲和力的生物活性合成类视黄醇。我们还报告了甲硅烷基化产物进一步转变为有用的衍生物的过程。
• Electrophilic ipso substitution of trimethylsilyl groups in fluorobenzenes
  作者：Paul L. Coe、Alison M. Stuart、David J. Moody

  DOI：10.1016/s0022-1139(98)00253-x

  日期：1998.10

  Using variants of literature methods 2,4- and 2,6- difluorophenyltrimethylsilanes have been bromodesilylated to the corresponding bromodifluorobenzenes in moderate to good yields, 3-bromo-2,6-difluorophenyltrimethylsilane afforded 1,3-dibromo-2,4-difluorobenzene whilst 1,3-difluoro-2,4-bis(trimethylsilyl)benzene yielded 3-bromo-2,6-difluorophenyltrimethylsilane Application of either the Eaborn or Chvalovsky methods of nitrodesilylation to 4-fluorophenyltrimethylsilane, 2,4-difluorophenyltrimethylsilane and 2,6-difluorophenyltrimethylsilane afforded largely the corresponding desilylated products together with products associated with initial protodesilylation, followed by nitration of the resulting fluorobenzenes. The results obtained show that ipso desilylation in the fluoroaromatic series does follow the expected pattern previously obtained in the hydrocarbon analogues. They also show that in some cases the formation of unusually substituted fluoroarenes can be achieved more readily than by the methods previously used. (C) 1998 Elsevier Science S.A. All rights reserved.
• Metalation of Nitroaromatics with in Situ Electrophiles
  作者：W. Cameron Black、Benoit Guay、Frank Scheuermeyer

  DOI：10.1021/jo961839t

  日期：1997.2.1