1-(二氟甲基)-2,4,6-三甲基苯 | 103383-72-8

• 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-(二氟甲基)-2,4,6-三甲基苯
• 英文名称: 2-(difluoromethyl)-1,3,5-trimethylbenzene
• 英文别名: 2-(Difluoromethyl)mesitylene
• CAS: 103383-72-8
• 化学式: C₁₀H₁₂F₂
• 分子量: 170.202
• InChiKey: CYLWLDXFQINILA-UHFFFAOYSA-N

物化性质

• 沸点：
  205.8±35.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-mesityl-1,3-dithiolane 在 N-碘代丁二酰亚胺 、 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以55%的产率得到1-(二氟甲基)-2,4,6-三甲基苯
  参考文献：
  名称：

  Gem-Difluoro compounds: a convenient preparation from ketones and aldehydes by halogen fluoride treatment of 1,3-dithiolanes

  摘要：

  DOI：

  10.1021/jo00368a022

文献信息

• Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes
  作者：Shaozhong Ge、Wojciech Chaładaj、John F. Hartwig

  DOI：10.1021/ja501117v

  日期：2014.3.19

  α-difluoroketones with aryl and heteroaryl bromides and chlorides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)Cy2 as ligand. The combination of this Pd-catalyzed arylation and base-induced cleavage of the acyl–aryl C–C bond within the α-aryl-α,α-difluoroketone constitutes a one-pot, two-step procedure to synthesize difluoromethylarenes from aryl halides. A broad range

  我们报告了 Pd 催化的 α,α-二氟酮与芳基和杂芳基溴化物和氯化物的 α-芳基化反应，该反应由含有 P(t-Bu)Cy2 作为配体的空气和水分稳定的钯环络合物催化。这种 Pd 催化的芳基化和碱诱导的 α-芳基-α,α-二氟酮内酰基-芳基 C-C 键断裂的组合构成了从芳基卤化物合成二氟甲基芳烃的一锅两步法。广泛的电子变化芳基和杂芳基溴化物和氯化物经历了这两种转化，以高产率提供了 α-芳基-α,α-二氟酮、二氟甲基芳烃和二氟甲基杂芳烃。
• Sandmeyer Difluoromethylation of (Hetero-)Arenediazonium Salts
  作者：Christian Matheis、Kévin Jouvin、Lukas J. Goossen

  DOI：10.1021/ol5030037

  日期：2014.11.21

  straightforward conversion of (hetero-)arenediazonium salts into the corresponding difluoromethyl (hetero-)arenes under mild conditions. The actual difluoromethylating reagent, a difluoromethyl–copper complex, is formed in situ from copper thiocyanate and TMS–CF2H. The diazonium salts are either preformed or generated in situ from broadly available aromatic amines.

  已经开发了Sandmeyer型二氟甲基化方法，其允许在温和的条件下将（杂）芳烯二鎓盐直接转化为相应的二氟甲基（杂）芳烃。实际的二氟甲基化试剂，即二氟甲基-铜络合物，是由硫氰酸铜和TMS-CF 2 H原位形成的。重氮盐既可以预先形成，也可以由广泛使用的芳族胺原位生成。
• Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent
  作者：Kohsuke Aikawa、Hiroki Serizawa、Koki Ishii、Koichi Mikami

  DOI：10.1021/acs.orglett.6b01734

  日期：2016.8.5

  The palladium-catalyzed Negishi cross-coupling reaction of aryl iodides and bromides with (difluoromethyl)zinc reagent bearing a diamine such as TMEDA is achieved to provide the difluoromethylated aromatic compounds in good to excellent yields. The advantages of (difluoromethyl)zinc reagent are that (1) the derivatives, which possess different stability and reactivity, can be readily prepared via ligand

  芳基碘化物和溴化物与带有二胺的（二氟甲基）锌试剂（如TMEDA）的钯催化的Negishi交叉偶联反应可良好地提供二氟甲基化的芳族化合物，并获得优异的收率。（二氟甲基）锌试剂的优点是（1）具有不同稳定性和反应性的衍生物可以通过配体筛选容易地制备，并且（2）从锌试剂到钯催化剂的二氟甲基基团的金属转移有效地进行而无需激活剂。
• Well-Defined, Shelf-Stable (NHC)Ag(CF₂H) Complexes for Difluoromethylation
  作者：Yang Gu、Dalu Chang、Xuebing Leng、Yucheng Gu、Qilong Shen

  DOI：10.1021/acs.organomet.5b00350

  日期：2015.6.22

  The preparation of the thermally stable, well-defined NHC-ligated difluoromethylated silver complexes la,b is described. The complexes were fully characterized, and the structural assignments were ambiguously further confirmed by single-crystal X-ray diffraction. Reactions of [(SIPr)Ag(CF2H)] with a variety of activated electrophiles such as diaryliodonium salts, vinyl(aryl)iodonium salts, aryldiazonium salts, and acid chlorides in the presence or absence of CuI occurred smoothly at room temperature to generate difluoromethylated compounds in good to excellent yields.
• SONDEJ S. C.; KATZENELLENBOGEN J. A., J. ORG. CHEM., 51,(1986) N 18, 3508-8513
  作者：SONDEJ S. C.、 KATZENELLENBOGEN J. A.

  DOI：——

  日期：——