1-methyl-4-(phenylthio)-1,2,3,6-tetrahydropyridine | 144466-77-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methyl-4-(phenylthio)-1,2,3,6-tetrahydropyridine
• 英文别名: 1-methyl-4-phenylsulfanyl-3,6-dihydro-2H-pyridine
• CAS: 144466-77-3
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: PTPLGUWNXUCGAH-UHFFFAOYSA-N

物化性质

• 沸点：
  317.8±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(phenylthio)-1,2,3,6-tetrahydropyridine 在 吡啶 、 tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 1-Methyl-4-phenylsulfanyl-2,3-dihydropyridin-1-ium
  参考文献：
  名称：

  化学模型研究的单胺氧化酶B催化4-取代的1-甲基-1,2,3,6-四氢吡啶的氧化。

  摘要：

  已经提出了MAO-B催化的胺的α-碳氧化可通过单电子转移（SET）或氢原子转移（HAT）途径进行。为了试图区分这些途径，我们使用化学模型检查了一系列4-取代的1-甲基-1,2,3,6-四氢吡啶衍生物（为MAO-B底物的化合物）的α-碳氧化SET途径[使用Fe + 3（1,10-菲咯啉）3的PF-6盐作为电子受体]和HAT途径（使用叔丁氧基作为氢原子受体）。用这些化合物观察到的氧化和氘同位素速率与两个模型反应相似。因此，与它们在建模相关细胞色素P450催化的N，N-二甲基苯胺衍生物的α-碳氧化中的用途不同，

  DOI：

  10.1016/s0968-0896(97)00101-6
• 作为产物：
  描述：

  1-甲基-4-苯基硫基吡啶-1-鎓碘化物 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 1-methyl-4-(phenylthio)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 4-substituted 1-methyl-1,2,3,6-tetrahydropyridine analogs of MPTP

  摘要：

  The exceptionally good MAO-B substrate properties of several 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) derivatives have prompted studies to evaluate the corresponding properties of tetrahydropyridines bearing heteroatom-linked groups at C-4. The 1-methyl-4-phenoxy-1,2,3,6-tetrahydropyridine analog proved to be an excellent MAO-B substrate. Unlike analogs bearing hydrocarbon substituents at C-4, the resulting dihydropyridinium metabolite did not undergo further oxidation to the pyridinium compound but rather underwent hydrolytic cleavage. This observation has led to studies designed to explore the possibility of developing novel, nontoxic derivatives of MPTP bearing potential pharmacologically active leaving groups at C-4. In this paper we report the results of synthetic and metabolic studies on a series of tetrahydropyridine analogs of MPTP with oxygen, sulfur, and carbamoyloxy derivatives on C-4 which serve as model compounds to evaluate the scope of this prodrug concept.

  DOI：

  10.1021/jm00101a026

文献信息

• AZA-DIELS-ALDER REACTIONS OF 2-(PHENYLTHIO)-1,3-BUTADIENE WITH SIMPLE IMINIUM SALTS
  作者：Shang-Shing P. Chou、Chia-Cheng Hung

  DOI：10.1081/scc-100103543

  日期：2001.1

  The titled compound 2 was readily prepared by thermal desulfonylation of 3-(phenylthio)-3-sulfolene (1). The aza-Diels-Alder reactions of 2 with some simple iminium salts gave the cyclized products 3–7 in good yield with complete control of regiochemistry.

  通过3-(苯硫基)-3-环丁砜(1)的热脱磺酰化容易地制备标题化合物2。2 与一些简单的亚胺盐的 aza-Diels-Alder 反应在完全控制区域化学的情况下以良好的收率得到环化产物 3-7。
• Design, synthesis, and biological evaluation of novel 4-substituted 1-methyl-1,2,3,6-tetrahydropyridine analogs of MPTP
  作者：Zhiyang Zhao、Deepak Dalvie、Noreen Naiman、Kay Castagnoli、Neal Castagnoli

  DOI：10.1021/jm00101a026

  日期：1992.11

  The exceptionally good MAO-B substrate properties of several 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) derivatives have prompted studies to evaluate the corresponding properties of tetrahydropyridines bearing heteroatom-linked groups at C-4. The 1-methyl-4-phenoxy-1,2,3,6-tetrahydropyridine analog proved to be an excellent MAO-B substrate. Unlike analogs bearing hydrocarbon substituents at C-4, the resulting dihydropyridinium metabolite did not undergo further oxidation to the pyridinium compound but rather underwent hydrolytic cleavage. This observation has led to studies designed to explore the possibility of developing novel, nontoxic derivatives of MPTP bearing potential pharmacologically active leaving groups at C-4. In this paper we report the results of synthetic and metabolic studies on a series of tetrahydropyridine analogs of MPTP with oxygen, sulfur, and carbamoyloxy derivatives on C-4 which serve as model compounds to evaluate the scope of this prodrug concept.
• Chemical model studies on the monoamine oxidase-B catalyzed oxidation of 4-substituted 1-methyl-1,2,3,6-tetrahydropyridines
  作者：Christelle Franot、Stéphane Mabic、Neal Castagnoli

  DOI：10.1016/s0968-0896(97)00101-6

  日期：1997.8

  Fe+3 (1,10-phenanthroline)3 as the electron acceptor] and HAT pathway (using the tert-butoxyl radical as the hydrogen atom acceptor). The rates of oxidation and deuterium isotope effects observed with these compounds were similar with the two model reactions. Consequently, unlike their utility in modeling the related cytochrome P450 catalyzed alpha-carbon oxidation of N,N-dimethylaniline derivatives

  已经提出了MAO-B催化的胺的α-碳氧化可通过单电子转移（SET）或氢原子转移（HAT）途径进行。为了试图区分这些途径，我们使用化学模型检查了一系列4-取代的1-甲基-1,2,3,6-四氢吡啶衍生物（为MAO-B底物的化合物）的α-碳氧化SET途径[使用Fe + 3（1,10-菲咯啉）3的PF-6盐作为电子受体]和HAT途径（使用叔丁氧基作为氢原子受体）。用这些化合物观察到的氧化和氘同位素速率与两个模型反应相似。因此，与它们在建模相关细胞色素P450催化的N，N-二甲基苯胺衍生物的α-碳氧化中的用途不同，