α-difluoromethyldiphenyl acetonitrile | 1427-12-9

• 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: α-difluoromethyldiphenyl acetonitrile
• 英文别名: 3,3-difluoro-2,2-diphenylpropanenitrile；(2-difluoromethyl)diphenylacetonitrile；α-Difluormethyl-diphenyl-acetonitril；I+/--(Difluoromethyl)-I+/--phenylbenzeneacetonitrile
• CAS: 1427-12-9
• 化学式: C₁₅H₁₁F₂N
• 分子量: 243.256
• InChiKey: IEGNIHPOGPMTQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-difluoromethyldiphenyl acetonitrile 生成 α-Difluormethyl-diphenylessigsaeure
  参考文献：
  名称：

  Chlorodifluoromethane as a difluoromethylating agent

  摘要：

  DOI：

  10.1016/s0040-4039(01)99204-4
• 作为产物：
  描述：

  三氟甲烷 、 二苯乙腈 在 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.5h， 以30%的产率得到α-difluoromethyldiphenyl acetonitrile
  参考文献：
  名称：

  Use of fluoroform as a source of difluorocarbene in the synthesis of N -CF 2 H heterocycles and difluoromethoxypyridines

  摘要：

  Fluoroform is used as a source of difluorocarbene to convert various N-, O-, and C-nucleophiles to their difluoromethylated derivatives. Imidazole, benzimidazole, benztriazole, hydroxypyridines, and their derivatives underwent reaction at moderate temperatures and atmospheric pressure, using potassium hydroxide as base in a two-phase (water/acetonitrile) process to provide moderate to good yields of the respective products. Nitrophenols required addition of a co-solvent (methanol) to obtain good yields of products. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.08.015

文献信息

• α-Difluoromethylation on sp³ Carbon of Nitriles Using Fluoroform and Ruppert–Prakash Reagent
  作者：Kohsuke Aikawa、Kenichi Maruyama、Kazuya Honda、Koichi Mikami

  DOI：10.1021/acs.orglett.5b02438

  日期：2015.10.2

  Difluoromethylation on sp(3) carbon of various nitrile compounds with lithium base and fluoroform (CF3H), which is an ideal difluoromethylating reagent, is shown to provide the alpha-difluoromethylated nitrile products with an all-carbon quaternary center in moderate to high yields. The Ruppert-Prakash reagent (CF3TMS) is also applicable to the reaction, affording the alpha-siladifluoromethylated nitrile products, which can be utilized for sequential carbon carbon bond-forming reactions. These reactions using 1.1 equiv of lithium base, 1.5-2.0 equiv of CF3H or CF3TMS, and easily accessible nitrile derivatives are completed in only a few minutes, resulting in the formation of valuable difluoromethylated compounds.
• Difluoromethylation of some C–H acids with chlorodifluoromethane under conditions of phase transfer catalysis (PTC)
  作者：Ewelina Nawrot、Andrzej Jończyk

  DOI：10.1016/j.jfluchem.2009.02.008

  日期：2009.5

  Selected C-H acids react with difluorocarbene generated from chlorodifluoromethane with concentrated aqueous solution of sodium hydroxide, and a catalyst, benzyltriethylammonium chloride (TEBAC) in benzene or THF affording C-difluoromethyl substituted derivatives. This process is restricted to C-H acids of pK(a) congruent to 16.3-19.1. The observed facts are rationalized. (C) 2009 Elsevier B.V. All rights reserved.