(R)-1,2,3,4-tetrahydro-8-methoxy-N,N-dimethyl-5-[4-(trifluoromethyl)phenyl]-2-naphthaleneamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-1,2,3,4-tetrahydro-8-methoxy-N,N-dimethyl-5-[4-(trifluoromethyl)phenyl]-2-naphthaleneamine
• 英文别名: 5-[4-(Trifluoromethyl)phenyl]-8-methoxy-N,N-dimethyltetralin-2alpha-amine；(2R)-8-methoxy-N,N-dimethyl-5-[4-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalen-2-amine
• 化学式: C₂₀H₂₂F₃NO
• 分子量: 349.396
• InChiKey: OZZVJHBGGXHGPX-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-三氟甲基苯硼酸 、 (R)-5-bromo-1,2,3,4-tetrahydro-8-methoxy-N,N-dimethyl-2-haphthalenamine hydrobromide 在 polymer-supported palladium catalyst potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以69.4%的产率得到(R)-1,2,3,4-tetrahydro-8-methoxy-N,N-dimethyl-5-[4-(trifluoromethyl)phenyl]-2-naphthaleneamine
  参考文献：
  名称：

  A SIMPLE, RECYCLABLE, POLYMER-SUPPORTED PALLADIUM CATALYST FOR SUZUKI COUPLING—AN EFFECTIVE WAY TO MINIMIZE PALLADIUM CONTAMINATION

  摘要：

  To address the challenges encountered in homogeneous catalytic processes, such as the minimization of metal contamination and the recycling of the catalysts, a polymer-supported palladium catalyst for Suzuki coupling was developed. The application of this heterogeneous palladium catalyst to the synthesis of a novel, amino-tetralin type, pharmaceutical ingredient led to a very low residual palladium content (< 1.1 ppm).

  DOI：

  10.1081/scc-120003154

文献信息

• TETRALINES BEARING A PHENYL SUBSTITUANT ON THE AROMATIC RING AND THEIR USE IN THE TREATMENT OF EPILEPSY, STROKE AND BRAIN OR SPINAL TRAUMA
  申请人：Novartis AG

  公开号：EP0823892A1

  公开（公告）日：1998-02-18
• US6169116B1
  申请人：——

  公开号：US6169116B1

  公开（公告）日：2001-01-02
• [EN] TETRALINES BEARING A PHENYL SUBSTITUANT ON THE AROMATIC RING AND THEIR USE IN THE TREATMENT OF EPILEPSY, STROKE AND BRAIN OR SPINAL TRAUMA<br/>[FR] TETRALINES AYANT UN SUBSTITUANT PHENYLE SUR LE NOYAU AROMATIQUE ET UTILISATION DE CES TETRALINES DANS LE TRAITEMENT DE L'EPILEPSIE, DES ACCIDENTS CARDIOVASCULAIRES ET DES TRAUMATISMES DU CERVEAU OU DE LA MOELLE EPINIERE
  申请人：——

  公开号：WO1996034849A1

  公开（公告）日：1996-11-07

  [EN] Compounds of formula (I) wherein R1 and R2, independently, are hydrogen (C1-4)alkyl, (C1-4)alkoxy, (C1-4)alkylthio, halogen, trifluoromethyl, trifluoromethoxy, cyano, (C2-5)alkanoyl, (C1-4)alkylsulfonyl or sulfamoyl; R3 is hydrogen, hydroxy, (C1-4)alkyl, (C1-4)alkoxy, halogen, cyano, (C2-5)alkanoyl, carbamoyl, (C1-4)alkylsulfonyloxy or trifluoromethylsulfonyloxy; and R4 and R5, independently, are hydrogen, (C1-4)alkyl, hydroxy(C2-4)alkyl or phenyl(C1-4)alkyl, or form together with the nitrogen atom to which they are attached a pyrrolidinyl, piperidino or piperazinyl group, in free base or acid addition salt form. Compounds according to formula (I) are useful in the treatment of epilepsy, stroke and brain or spinal trauma.
  [FR] Cette invention concerne des composés correspondant à la formule (I), où R1 et R2 représentent indépendamment hydrogène, alkyle (C1-4), alcoxy (C1-4), alkylthio (C1-4), halogène, trifluorométhyle, trifluorométhoxy, cyano, alcanoyle (C2-5), alkyl (C1-4) sulfonyle, ou sulfamoyle; R3 représente hydrogène, hydroxy, alkyle (C1-4), alcoxy (C1-4), halogène, cyano, alcanoyle (C2-5), carbamoyle, alkyl (C1-4) sulfonyloxy ou trifluorométhylsulfonyloxy; et R4 et R5 représentent indépendamment hydrogène, alkyle (C1-4), hydroxyalkyle (C2-4), ou phényle-alkyle (C1-4), ou encore forment avec l'atome d'azote auquel ils sont attachés un groupe pyrrolidinyle, pipéridino ou pipérazinyle, en base libre ou sous forme de sel d'addition d'acide. Les composés correspondant à la formule (I) sont utiles dans le traitement de l'épilepsie, des accidents cardiovasculaires et des traumatismes du cerveau ou de la moelle épinière.
• A SIMPLE, RECYCLABLE, POLYMER-SUPPORTED PALLADIUM CATALYST FOR SUZUKI COUPLING—AN EFFECTIVE WAY TO MINIMIZE PALLADIUM CONTAMINATION
  作者：Wen-Chung Shieh、Ratna Shekhar、Thomas Blacklock、Anthony Tedesco

  DOI：10.1081/scc-120003154

  日期：2002.1

  To address the challenges encountered in homogeneous catalytic processes, such as the minimization of metal contamination and the recycling of the catalysts, a polymer-supported palladium catalyst for Suzuki coupling was developed. The application of this heterogeneous palladium catalyst to the synthesis of a novel, amino-tetralin type, pharmaceutical ingredient led to a very low residual palladium content (< 1.1 ppm).