1-乙基-4-(3-甲氧基苯基)-3,6-二氢-2H-吡啶 | 102538-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-乙基-4-(3-甲氧基苯基)-3,6-二氢-2H-吡啶
• 英文名称: 1,2,3,6-tetrahydro-4-(3-methoxyphenyl)-N-ethylpyridine
• 英文别名: 1-ethyl-4-hydroxy-4-(3-methoxyphenyl)-1,2,3,6-tetrhydropyridine；1-Ethyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine；1-ethyl-4-(3-methoxyphenyl)-3,6-dihydro-2H-pyridine
• CAS: 102538-16-9
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: DNDWVWSRWMEFQT-UHFFFAOYSA-N

物化性质

• 沸点：
  92-96 °C(Press: 0.1 Torr)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙基-4-(3-甲氧基苯基)-3,6-二氢-2H-吡啶 在 platinum(IV) oxide 盐酸 、 正丁基锂 、 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， -50.0~25.0 ℃ 、413.69 kPa 条件下， 反应 39.17h， 生成 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline
  参考文献：
  名称：

  Characterization of the neurotoxic potential of m-methoxy-MPTP and the use of its N-ethyl analog as a means of avoiding exposure to a possible Parkinson-causing agent

  摘要：

  1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2) produced persistent depletion of striatal dopamine in mice after four daily injections, although it was less potent than 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). MPTP has been implicated as a cause of Parkinsonism in drug abusers who inadvertently self-administered it and in industrial chemists who were exposed to it. Our results suggest that the m-methoxy compound has the same neurotoxic potential to cause destruction of nigrostriatal dopamine neurons that would lead to Parkinsonian symptoms in humans. In contrast, 1-ethyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (11) had no effects on striatal dopamine in mice, even at doses 8 times those of MPTP. A method of preparing 11 and using it as an intermediate in the synthesis of potential analgesic drugs, thus avoiding a potentially neurotoxic intermediate, is described.

  DOI：

  10.1021/jm00158a033
• 作为产物：
  描述：

  N-乙基-4-哌啶酮 在 正丁基锂 、 磷酸 作用下， 反应 5.5h， 生成 1-乙基-4-(3-甲氧基苯基)-3,6-二氢-2H-吡啶
  参考文献：
  名称：

  Characterization of the neurotoxic potential of m-methoxy-MPTP and the use of its N-ethyl analog as a means of avoiding exposure to a possible Parkinson-causing agent

  摘要：

  1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2) produced persistent depletion of striatal dopamine in mice after four daily injections, although it was less potent than 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). MPTP has been implicated as a cause of Parkinsonism in drug abusers who inadvertently self-administered it and in industrial chemists who were exposed to it. Our results suggest that the m-methoxy compound has the same neurotoxic potential to cause destruction of nigrostriatal dopamine neurons that would lead to Parkinsonian symptoms in humans. In contrast, 1-ethyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (11) had no effects on striatal dopamine in mice, even at doses 8 times those of MPTP. A method of preparing 11 and using it as an intermediate in the synthesis of potential analgesic drugs, thus avoiding a potentially neurotoxic intermediate, is described.

  DOI：

  10.1021/jm00158a033

文献信息

• Treatment of pruritus
  申请人：Pfizer Inc.

  公开号：US05972962A1

  公开（公告）日：1999-10-26

  The use of certain known 1,3,4 trisubstituted 4-aryl-piperidines for the treatment of pruritus in humans and animals is disclosed.

  揭示了利用某些已知的1,3,4-三取代基的4-芳基哌啶类化合物用于治疗人类和动物的瘙痒症状。
• Synthesis of 9β-methyl-2-alkyl-7-oxo-5-arylmorphans
  作者：James B. Thomas、Xiaoling Zheng、Lawrence E. Brieaddy、Jason P. Burgess、S. Wayne Mascarella、Scott E. Fix、Buddy E. Cantrell、Dennis M. Zimmerman、F. Ivy Carroll

  DOI：10.1016/s0040-4039(98)01549-4

  日期：1998.9

  synthetic approach to 9β-methyl-2-alkyl-7-oxo-5-arylmorphans has been developed utilizing alkylation of the metalloenamine of 1,2,3,6-tetrahydro-4-aryl-1-alkylpyridines with 2-(chloromethyl)-3,5-dioxahex-1-ene (Okahara's reagent).

  利用1,2,3,6-四氢-4-芳基-1-烷基吡啶的金属烯胺与2-（-氯甲基）-3,5-二恶己基-1-烯（冈原试剂）。
• ZIMMERMAN D. M.; CANTRELL B. E.; REEL J. K.; HEMRICK-LUECKE S. K.; FULLER+, J. MED. CHEM., 29,(1986) N 8, 1517-1520
  作者：ZIMMERMAN D. M.、 CANTRELL B. E.、 REEL J. K.、 HEMRICK-LUECKE S. K.、 FULLER+

  DOI：——

  日期：——
• US5972962A
  申请人：——

  公开号：US5972962A

  公开（公告）日：1999-10-26
• Characterization of the neurotoxic potential of m-methoxy-MPTP and the use of its N-ethyl analog as a means of avoiding exposure to a possible Parkinson-causing agent
  作者：Dennis M. Zimmerman、Buddy E. Cantrell、Jon K. Reel、Susan K. Hemrick-Luecke、Ray W. Fuller

  DOI：10.1021/jm00158a033

  日期：1986.8

  1-Methyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (2) produced persistent depletion of striatal dopamine in mice after four daily injections, although it was less potent than 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). MPTP has been implicated as a cause of Parkinsonism in drug abusers who inadvertently self-administered it and in industrial chemists who were exposed to it. Our results suggest that the m-methoxy compound has the same neurotoxic potential to cause destruction of nigrostriatal dopamine neurons that would lead to Parkinsonian symptoms in humans. In contrast, 1-ethyl-4-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (11) had no effects on striatal dopamine in mice, even at doses 8 times those of MPTP. A method of preparing 11 and using it as an intermediate in the synthesis of potential analgesic drugs, thus avoiding a potentially neurotoxic intermediate, is described.