[1]Naphthyl-[4]pyridyl-methanol | 108771-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1]Naphthyl-[4]pyridyl-methanol
• 英文别名: Naphthalen-1-yl(pyridin-4-yl)methanol
• CAS: 108771-13-7
• 化学式: C₁₆H₁₃NO
• mdl: MFCD17126118
• 分子量: 235.285
• InChiKey: IKCXCDKPIMSHGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C
• 沸点：
  451.4±30.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1]Naphthyl-[4]pyridyl-methanol 在 sodium tetrahydroborate 、 甲酸 、 锌 作用下， 反应 48.0h， 生成 1-Methyl-4-naphthalen-1-ylmethyl-1,2,3,6-tetrahydro-pyridine
  参考文献：
  名称：

  Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analog: synthesis and monoamine oxidase catalyzed bioactivation

  摘要：

  Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.

  DOI：

  10.1021/jm00174a007
• 作为产物：
  描述：

  phenyl 4-pyridyl sulfoxide 在 苯基溴化镁 作用下， 反应 0.5h， 生成 [1]Naphthyl-[4]pyridyl-methanol
  参考文献：
  名称：

  吡啶基和喹啉基亚砜与格氏试剂的反应：吡啶基和喹啉基格氏试剂的便捷制备

  摘要：

  通过相应的苯亚砜与PhMgBr的反应生成3-，4-吡啶基和4-喹啉基格利雅试剂，并在用各种醛和酮处理后得到加合物。研究了反应的立体化学。

  DOI：

  10.1016/s0040-4039(00)83910-6

文献信息

• Ghigi, Chemische Berichte, 1942, vol. 75, p. 764,772
  作者：Ghigi

  DOI：——

  日期：——
• EFANGE, S. M. N.;MICHELSON, R. H.;REMMEL, R. P.;BOUDREAU, R. J.;DUTTA, A.+, J. MED. CHEM., 33,(1990) N2, C. 3133-3138
  作者：EFANGE, S. M. N.、MICHELSON, R. H.、REMMEL, R. P.、BOUDREAU, R. J.、DUTTA, A.+

  DOI：——

  日期：——
• FURUKAWA NAOMICHI; SHIBUTANI TADAO; MATSUMURA KAZUNORI; FUJIHARA HISASHI;+, TETRAHEDRON LETT., 27,(1986) N 33, 3899-3902
  作者：FURUKAWA NAOMICHI、 SHIBUTANI TADAO、 MATSUMURA KAZUNORI、 FUJIHARA HISASHI、+

  DOI：——

  日期：——
• US4246268A
  申请人：——

  公开号：US4246268A

  公开（公告）日：1981-01-20
• Flexible N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analog: synthesis and monoamine oxidase catalyzed bioactivation
  作者：S. Mbera Ngale Efange、R. H. Michelson、R. P. Remmel、R. J. Boudreau、A. K. Dutta、A. Freshler

  DOI：10.1021/jm00174a007

  日期：1990.12

  Eighteen analogues of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were synthesized and evaluated as substrates of monoamine oxidase. In general, the flexible analogues, characterized by the presence of a methylene (or ethylene) bridge between the aryl/heteroaryl and tetrahydropyridyl moieties, were better substrates of the enzyme than the conformationally restricted MPTP. It is suggested that the increased oxidative activity of these flexible analogues reflects enhanced binding due to the ability of the C-4-aryl/heteroaryl substituent to gain access to a hydrophobic pocket within the substrate binding site.