2,3,6-trifluorophenylacetyl chloride | 1231932-49-2

• 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: 2,3,6-trifluorophenylacetyl chloride
• 英文别名: 2,3,6-Trifluorophenylacetyl chloride；2-(2,3,6-trifluorophenyl)acetyl chloride
• CAS: 1231932-49-2
• 化学式: C₈H₄ClF₃O
• 分子量: 208.567
• InChiKey: VTPTXURNHFDQMK-UHFFFAOYSA-N

物化性质

• 沸点：
  213.2±40.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,6-trifluorophenylacetyl chloride 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-(4-methylpiperazin-1-yl)-N-[5-[2-(2,3,6-trifluorophenyl)acetyl]-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-3-yl]benzamide
  参考文献：
  名称：

  The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing

  摘要：

  New drugs for neglected tropical diseases such as human African trypanosomiasis (HAT) are needed, yet drug discovery efforts are not often focused on this area due to cost. Target repurposing, achieved by the matching of essential parasite enzymes to those human enzymes that have been successfully inhibited by small molecule drugs, provides an attractive means by which new drug optimization programs can be pragmatically initiated. In this report we describe our results in repurposing an established class of human Aurora kinase inhibitors, typified by danusertib (1), which we have observed to be an inhibitor of trypanosomal Aurora kinase 1 (TbAUK1) and effective in parasite killing in vitro. Informed by homology modeling and docking, a series of analogs of I were prepared that explored the scope of the chemotype and provided a nearly 25-fold improvement in cellular selectivity for parasite cells over human cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.038
• 作为产物：
  描述：

  2,3,6-三氟苯基乙酸 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 醋酸异丙酯 为溶剂， 反应 1.0h， 生成 2,3,6-trifluorophenylacetyl chloride
  参考文献：
  名称：

  [EN] PROCESS FOR MAKING CGRP RECEPTOR ANTAGONISTS
  [FR] PROCÉDÉ DE FABRICATION D'ANTAGONISTES DE RÉCEPTEURS DU CGRP

  摘要：

  该披露涵盖了一种用于制备哌啶酮羧酰胺茚和氮杂茚衍生物的新型过程，与以往的合成方法相比，该过程步骤更少，产率更高。这些化合物是CGRP受体拮抗剂，可用于治疗偏头痛。酰胺键形成的条件包括例如将化合物B（盐断裂后）和C与酰胺偶联试剂以及可选的添加剂和酸和/或碱在非反应性溶剂中反应。

  公开号：

  WO2013169348A1

文献信息

• [EN] PROCESS FOR MAKING CGRP RECEPTOR ANTAGONISTS<br/>[FR] PROCÉDÉ DE FABRICATION D'ANTAGONISTES DE RÉCEPTEURS DU CGRP
  申请人：MERCK SHARP & DOHME

  公开号：WO2013169348A1

  公开（公告）日：2013-11-14

  The disclosure encompasses a novel process for making piperidinone carboxamide indane and azainane derivatives, having less steps and improved yields as compared to previous synthetic methods for making these compounds, which are CGRP receptor antagonists, useful for the treatment of migrane. Conditions for an amide bond formation between an acid and amine include for example reacting the compounds of Formulae B (after salt break) and C with an amide coupling reagent and optionally an additive and an acid and/or a base in a non-reactive solvent.

  该披露涵盖了一种用于制备哌啶酮羧酰胺茚和氮杂茚衍生物的新型过程，与以往的合成方法相比，该过程步骤更少，产率更高。这些化合物是CGRP受体拮抗剂，可用于治疗偏头痛。酰胺键形成的条件包括例如将化合物B（盐断裂后）和C与酰胺偶联试剂以及可选的添加剂和酸和/或碱在非反应性溶剂中反应。
• HERBICIDALLY AND INSECTICIDALLY ACTIVE 4-PHENYL-SUBSTITUTED PYRIDAZINONES
  申请人：LEHR Stefan

  公开号：US20100173775A1

  公开（公告）日：2010-07-08

  The invention describes phenyl-substituted pyridazinones of the formula (I) as herbicides and insecticides. In this formula (I), A, B, G, X, Y and Z are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen, nitro and cyano.

  该发明描述了公式（I）中的苯基取代的吡啪唑酮作为除草剂和杀虫剂。在此公式（I）中，A，B，G，X，Y和Z是诸如氢，烷基等有机基团和卤素，硝基和氰基等其他基团。
• Herbicidally and insecticidally active 4-phenyl-substituted pyridazinones
  申请人：Bayer Cropscience AG

  公开号：US08188008B2

  公开（公告）日：2012-05-29

  The invention describes phenyl-substituted pyridazinones of the formula (I) as herbicides and insecticides. In this formula (I), A, B, G, X, Y and Z are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen, nitro and cyano.

  该发明描述了公式（I）的苯基取代的吡啪啶酮作为除草剂和杀虫剂。在该公式（I）中，A、B、G、X、Y和Z是氢、有机基团如烷基和其他基团如卤素、硝基和氰基等基团。
• US8188008B2
  申请人：——

  公开号：US8188008B2

  公开（公告）日：2012-05-29
• The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing
  作者：Stefan O. Ochiana、Vidya Pandarinath、Zhouxi Wang、Rishika Kapoor、Mary Jo Ondrechen、Larry Ruben、Michael P. Pollastri

  DOI：10.1016/j.ejmech.2012.07.038

  日期：2013.4

  New drugs for neglected tropical diseases such as human African trypanosomiasis (HAT) are needed, yet drug discovery efforts are not often focused on this area due to cost. Target repurposing, achieved by the matching of essential parasite enzymes to those human enzymes that have been successfully inhibited by small molecule drugs, provides an attractive means by which new drug optimization programs can be pragmatically initiated. In this report we describe our results in repurposing an established class of human Aurora kinase inhibitors, typified by danusertib (1), which we have observed to be an inhibitor of trypanosomal Aurora kinase 1 (TbAUK1) and effective in parasite killing in vitro. Informed by homology modeling and docking, a series of analogs of I were prepared that explored the scope of the chemotype and provided a nearly 25-fold improvement in cellular selectivity for parasite cells over human cells. (C) 2012 Elsevier Masson SAS. All rights reserved.