2-(2,2-二氟丙基)异吲哚-1,3-二酮 | 1017241-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 2-(2,2-二氟丙基)异吲哚-1,3-二酮
• 英文名称: 2-(2,2-difluoropropyl)isoindoline-1,3-dione
• 英文别名: 2-(2,2-difluoropropyl)isoindole-1,3-dione
• CAS: 1017241-19-8
• 化学式: C₁₁H₉F₂NO₂
• 分子量: 225.195
• InChiKey: CTKPAUQAXMHVDE-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  299.3±35.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,2-二氟丙基)异吲哚-1,3-二酮 在 盐酸 作用下， 以 水 为溶剂， 反应 48.0h， 以20 g的产率得到2,2-二氟丙胺盐酸盐
  参考文献：
  名称：

  Discovery of 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-6,7-dihydro-2H-pyrazolo[3,4-f][1,4]oxazepin-8(5H)-one (PF-514273), a Novel, Bicyclic Lactam-Based Cannabinoid-1 Receptor Antagonist for the Treatment of Obesity

  摘要：

  We report the design, synthesis, and structure-activity relationships of novel bicyclic lactam-based cannabinoid type 1 (CB,) receptor antagonists. Members of these series are potent, selective antagonists in in vitro/in vivo efficacy models of CB, antagonism and exhibit robust oral activity in rodent models of food intake. These efforts led to the identification of 19d, which has been advanced to human clinical trials for weight management.

  DOI：

  10.1021/jm900255t
• 作为产物：
  描述：

  N-丙酮基邻苯二甲酰亚胺 在 二乙胺基三氟化硫 作用下， 反应 66.0h， 以36 g的产率得到2-(2,2-二氟丙基)异吲哚-1,3-二酮
  参考文献：
  名称：

  Discovery of 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-6,7-dihydro-2H-pyrazolo[3,4-f][1,4]oxazepin-8(5H)-one (PF-514273), a Novel, Bicyclic Lactam-Based Cannabinoid-1 Receptor Antagonist for the Treatment of Obesity

  摘要：

  We report the design, synthesis, and structure-activity relationships of novel bicyclic lactam-based cannabinoid type 1 (CB,) receptor antagonists. Members of these series are potent, selective antagonists in in vitro/in vivo efficacy models of CB, antagonism and exhibit robust oral activity in rodent models of food intake. These efforts led to the identification of 19d, which has been advanced to human clinical trials for weight management.

  DOI：

  10.1021/jm900255t

文献信息

• <i>gem</i>-Difluorination of Aminoalkynes via Highly Reactive Dicationic Species in Superacid HF−SbF₅:  Application to the Efficient Synthesis of Difluorinated Cinchona Alkaloid Derivatives
  作者：Anne-Céline Cantet、Hélène Carreyre、Jean-Pierre Gesson、Marie-Paule Jouannetaud、Brigitte Renoux

  DOI：10.1021/jo702441p

  日期：2008.4.1

  reacted in the superacid system HF−SbF5 to give regioselectively new β-gem-difluoroamines. The reaction, which is not observed in pure HF, is consistent with the formation of a dicationic intermediate (i.e., both vinylic and adjacent protonated N-ammonium cations). Application to the regioselective and efficient synthesis of difluorinated cinchona alkaloid derivatives is described.

  各种烷基化的胺，酰胺和酰亚胺在超酸体系HF-SbF 5中反应，生成区域选择性的新β-锗-二氟胺。在纯HF中未观察到的反应与双官能中间体（即乙烯基和相邻的质子化N-铵阳离子）的形成是一致的。描述了在区域选择性和有效合成二氟化金鸡纳生物碱衍生物中的应用。
• Selective Synthesis of <i>gem</i>-Chlorofluorinated Nitrogen-Containing Derivatives after Superelectrophilic Activation in Superacid HF/SbF₅
  作者：Fei Liu、Agnès Martin-Mingot、Marie-Paule Jouannetaud、Christian Bachmann、Gilles Frapper、Fabien Zunino、Sébastien Thibaudeau

  DOI：10.1021/jo102225w

  日期：2011.3.4

  The first direct selective synthesis of novel gem-chloro-fluorinated nitrogen-containing building blocks in super-acid is reported. The dramatic role of the chlorine atom on the reaction is shown by in situ NMR experiments and allows the involvement of a novel original superelectrophilic activation process in superacid HF/SbF5 to be postulated.