alpha-(2-吡啶基)-2,8-双(三氟甲基)-4-喹啉乙腈 | 83012-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: alpha-(2-吡啶基)-2,8-双(三氟甲基)-4-喹啉乙腈
• 中文别名: ALPHA-(2-吡啶基)-2,8-双(三氟甲基)-4-喹啉乙腈
• 英文名称: α-(2-Pyridyl)-2,8-bis(trifluoromethyl)-4-quinolylacetonitrile
• 英文别名: α,2-pyridinyl-2,8-bis(trifluoromethyl)-4-quinolineacetonitrile；alpha,2-Pyridyl-2,8-bis(trifluoromethyl)quinoline-4-acetonitrile；2-[2,8-bis(trifluoromethyl)quinolin-4-yl]-2-pyridin-2-ylacetonitrile
• CAS: 83012-12-8
• 化学式: C₁₈H₉F₆N₃
• 分子量: 381.28
• InChiKey: WCAXLPSKVMAJSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  418.5±40.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 海关编码：
  2933990090
• WGK Germany：
  3
• 危险标志：
  GHS06
• 危险性描述：
  H301,H413
• 危险性防范说明：
  P301 + P310

反应信息

• 作为反应物：
  描述：

  alpha-(2-吡啶基)-2,8-双(三氟甲基)-4-喹啉乙腈 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 0.84h， 生成 双[2,8-二(三氟甲基)喹啉-4-基-2-吡啶基]酮
  参考文献：
  名称：

  A straightforward mid high yielding synthesis of mefloquine -II.

  摘要：

  A new practical and high yielding synthesis of mefloquine (1) is described. Heteroarylation of 2-pyridylacetonitrile (2) gave the key intermediate 2-pyridyl-4-quinolylacetonitrile 4, which, on reaction with m-chloroperbenzoic acid, gave unexpectedly the cyanhydrine 5. The later, after base treatment afforded quantitatively the ketone 6.

  DOI：

  10.1016/s0040-4020(01)88284-3
• 作为产物：
  描述：

  2,8-双(三氟甲基)-4-羟基喹啉 在 sodium hydride 、 三氯氧磷 作用下， 反应 5.0h， 生成 alpha-(2-吡啶基)-2,8-双(三氟甲基)-4-喹啉乙腈
  参考文献：
  名称：

  A straightforward mid high yielding synthesis of mefloquine -II.

  摘要：

  A new practical and high yielding synthesis of mefloquine (1) is described. Heteroarylation of 2-pyridylacetonitrile (2) gave the key intermediate 2-pyridyl-4-quinolylacetonitrile 4, which, on reaction with m-chloroperbenzoic acid, gave unexpectedly the cyanhydrine 5. The later, after base treatment afforded quantitatively the ketone 6.

  DOI：

  10.1016/s0040-4020(01)88284-3

文献信息

• ONE POT SYNTHESIS OF [2, 8-BIS (TRIFLUOROMETHYL)-4- QUINOLINYL]2-PYRIDINYLMETHANONE, A MEFLOQUINE INTERMEDIATE
  申请人：NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH

  公开号：US20020188129A1

  公开（公告）日：2002-12-12

  The present invention provides a simple single step process for the preparation of [2,8-bis (trifluoromethyl)-4-quinolinyl]-2 -pyridinylmethanone, comprising the step of condensing a halo-quinoline with an alpha-picolyl derivatives in the presence of a solvent, a base and a phase transfer catalyst at −10° C. to +90° C.

  本发明提供了一种简单的单步制备[2,8-双(三氟甲基)-4-喹啉基]-2-吡啶基甲酮的方法，包括在溶剂、碱和相转移催化剂存在下，在-10℃至+90℃的条件下将卤代喹啉与α-哌啶基衍生物缩合的步骤。
• US6500955B1
  申请人：——

  公开号：US6500955B1

  公开（公告）日：2002-12-31
• [EN] PENTAFLUOROSULFANYL ANALOGS OF MEFLOQUINE<br/>[FR] ANALOGUES DE PENTAFLUOROSULFANYLE DE LA MÉFLOQUINE
  申请人：US OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE ARMY ON BEHALF OF U S ARMY MEDICAL RES AND MATE

  公开号：WO2010144102A1

  公开（公告）日：2010-12-16

  The present invention relates to new mefloquine derivatives and therapeutic compositions comprising one or more mefloquine derivatives. Mefloquine derivatives of the invention have at least one pentafluorosulfanyl moiety substitution at the 6 or 7 or 8 position. Certain mefloquine derivatives further include a quinoline methonal moiety substitution at the 4 position. These compositions are useful in the reduction, treatment, or prevention of malaria, microbial, parasitic, protozoan, bacterial, and fungal diseases and conditions. Advantageously, compositions of the invention are less able to cross the blood-brain barrier than mefloquine and as a result produce fewer adverse side effects to the central nervous system as compared to mefloquine.
• [EN] DERIVATIVES OF MEFLOQUINE AND ASSOCIATED METHODS FOR MAKING AND USING<br/>[FR] DÉRIVÉS DE LA MÉFLOQUINE ET PROCÉDÉS ASSOCIÉS DE RÉALISATION ET D'UTILISATION
  申请人：US OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE ARMY ON BEHALF OF U S

  公开号：WO2010144434A1

  公开（公告）日：2010-12-16

  The present invention relates to new mefloquine derivatives and therapeutic compositions comprising one or more mefloquine derivatives. Mefloquine derivatives of the invention have a pentafluorosulfanyl moiety substitution at the 8-position. Certain mefloquine derivatives further include a quinoline methanol moiety substitution at the 4-position. The present invention also relates to new intermediate compounds useful in the synthesis of the mefloquine derivatives, which intermediates also have a pentafluorosulfanyl moiety substitution at the 8-position.