1-cyclopropyl-4-(2-methylphenyl)-2,3-dihydropyridinium | 163632-19-7

• 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: 1-cyclopropyl-4-(2-methylphenyl)-2,3-dihydropyridinium
• 英文别名: 1-Cyclopropyl-4-(2-methylphenyl)-2,3-dihydropyridin-1-ium
• CAS: 163632-19-7
• 化学式: C₁₅H₁₈N
• 分子量: 212.315
• InChiKey: DGIMOPRHDRPRRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-4-(2-methylphenyl)-2,3-dihydropyridinium 在 硼氘化钠 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 1-cyclopropyl-4-(2-methylphenyl)-1,2,3,6-tetrahydropyridine-6-d₁
  参考文献：
  名称：

  Probing the Mechanism of Bioactivation of MPTP Type Analogs by Monoamine Oxidase B: Structure-Activity Studies on Substituted 4-Phenoxy-, 4-Phenyl-, and 4-Thiophenoxy-1-cyclopropyl-1,2,3,6-tetrahydropyridines

  摘要：

  Previous studies have shown that 4-benzyl-1-cyclopropyl-1,2,3,6-tetrahydropyridine is an excellent monoamine oxidase B (MAO-B) substrate (k(cat)/K-M = 1538 min(-1) mM(-1)) although the corresponding 4-phenyl analog displays MAO-B inactivating properties only. This behavior led us to speculate that the pathway for the MAO-B catalyzed oxidation of these tetrahydropyridines may not necessarily proceed via an initial single electron transfer step as proposed by others but rather through an initial alpha-carbon hydrogen atom abstraction step. In the present studies we have examined the interactions of various 4-phenoxy-, 4-phenyl-, and 4-thiophenoxy-1-cyclopropyl-1,2,3,6-tetrahydropyridine derivatives, some of which bear substituents on the phenyl ring. The 4-thiophenoxy- and all of the 4-phenoxytetrahydropyridine derivatives proved to be substrates but not inactivators of MAO-B, while several of the 4-phenyltetrahydropyridine derivatives were inactivators but not substrates. A case of particular interest was 1-cyclopropyl-4-(2-methylphenyl)-1,2,3,6-tetrahydropyridine, which displayed only substrate properties. The results are discussed in terms of two catalytic pathways, one of which involves partitioning of the proposed cyclopropylaminyl radical cation intermediate between cyclopropyl ring opening and proton loss while the second involves partitioning of the parent amine between an initial single electron transfer step, leading to cyclopropylaminyl radical cation formation and enzyme inactivation, and an initial alpha-carbon hydrogen atom abstraction step, leading to an allylic radical and dihydropyridinium product formation.

  DOI：

  10.1021/tx00047a010
• 作为产物：
  描述：

  1-环丙基-4-哌啶酮 在 盐酸 、 碘 、 magnesium 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 5.83h， 生成 1-cyclopropyl-4-(2-methylphenyl)-2,3-dihydropyridinium
  参考文献：
  名称：

  Probing the Mechanism of Bioactivation of MPTP Type Analogs by Monoamine Oxidase B: Structure-Activity Studies on Substituted 4-Phenoxy-, 4-Phenyl-, and 4-Thiophenoxy-1-cyclopropyl-1,2,3,6-tetrahydropyridines

  摘要：

  Previous studies have shown that 4-benzyl-1-cyclopropyl-1,2,3,6-tetrahydropyridine is an excellent monoamine oxidase B (MAO-B) substrate (k(cat)/K-M = 1538 min(-1) mM(-1)) although the corresponding 4-phenyl analog displays MAO-B inactivating properties only. This behavior led us to speculate that the pathway for the MAO-B catalyzed oxidation of these tetrahydropyridines may not necessarily proceed via an initial single electron transfer step as proposed by others but rather through an initial alpha-carbon hydrogen atom abstraction step. In the present studies we have examined the interactions of various 4-phenoxy-, 4-phenyl-, and 4-thiophenoxy-1-cyclopropyl-1,2,3,6-tetrahydropyridine derivatives, some of which bear substituents on the phenyl ring. The 4-thiophenoxy- and all of the 4-phenoxytetrahydropyridine derivatives proved to be substrates but not inactivators of MAO-B, while several of the 4-phenyltetrahydropyridine derivatives were inactivators but not substrates. A case of particular interest was 1-cyclopropyl-4-(2-methylphenyl)-1,2,3,6-tetrahydropyridine, which displayed only substrate properties. The results are discussed in terms of two catalytic pathways, one of which involves partitioning of the proposed cyclopropylaminyl radical cation intermediate between cyclopropyl ring opening and proton loss while the second involves partitioning of the parent amine between an initial single electron transfer step, leading to cyclopropylaminyl radical cation formation and enzyme inactivation, and an initial alpha-carbon hydrogen atom abstraction step, leading to an allylic radical and dihydropyridinium product formation.

  DOI：

  10.1021/tx00047a010

文献信息

• Decyclopropylation of 1-cyclopropyl-4-hydroxy-4-(2-methylphenyl)piperidine N-oxide
  作者：You-Xiong Wang、Neal Castagnoli

  DOI：10.1016/0040-4039(95)00693-7

  日期：1995.6

  anhydride (TFAA) yields the corresponding descyclopropyl secondary amine in excellent yield. This reaction may serve as a model for the mechanism based inactivation of monoamine oxidase B (MAO-B) by cyclopropylamines which recently has been proposed to proceed via a polar mechanism involving a flavin-amine adduct.

  用三氟乙酸酐（TFAA）处理1-环丙基-4-羟基-4-（2-甲基苯基）哌啶N-氧化物可产生相应的脱环丙基仲胺，产率极高。该反应可以用作环丙胺使单胺氧化酶B（MAO-B）失活的机理模型，最近已提出该反应是通过涉及黄素-胺加合物的极性机理进行的。