1-(2-pyridyl)-1,2-ethanediol hydrochloride | 51594-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(2-pyridyl)-1,2-ethanediol hydrochloride
• 英文别名: 1-pyridin-2-yl-ethane-1,2-diol; hydrochloride；1-(Pyridin-2-yl)ethane-1,2-diol hydrochloride；1-pyridin-2-ylethane-1,2-diol;hydrochloride
• CAS: 51594-24-2
• 化学式: C₇H₉NO₂*ClH
• 分子量: 175.615
• InChiKey: UQYDVJUHPWTDHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-pyridyl)-1,2-ethanediol hydrochloride 在 盐酸 作用下， 生成 2,2-Diphenyl-4-(1-benzyl-2-pyridyl)-1,3-dioxolan
  参考文献：
  名称：

  Synthesis of tritium and carbon-14 labeled 1, 3-dioxolanes

  摘要：

  将二甲氧基二苯甲烷 14C （III）与 2-(2-哌啶基)-1，2-乙二醇盐酸盐的左旋（IIa）和右旋（IIb）异构体缩合、2-二苯基-4-(2-哌啶基)-1, 3-二氧戊环盐酸盐，生成碳-14 标记的二氧戊环 Ic 和 Id，并在非对称碳原子上保留构型。逐步还原 2,2-二苯基 1-4-(1-苄基-1-2-吡啶 1)-1,3-二氧戊环。分离出熔点较低的外消旋体异构体二酒石酸盐（If），并进行解析，得到具有光学活性的氚标记的二氧戊环 Ig 和 Ih。

  DOI：

  10.1002/jlcr.2590090306
• 作为产物：
  描述：

  2-oxiranylpyridine 在 三氟甲磺酸 、 chloride ion exchange resin XAD-400 、 水 作用下， 生成 1-(2-pyridyl)-1,2-ethanediol hydrochloride
  参考文献：
  名称：

  Analogs of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure activity relationships

  摘要：

  A series of dioxolane analogues based on dexoxadrol ((4S,6S)-2,2-diphenyl-4-(2-piperidyl)-1,3-dioxolane) and etoxadrol ((2S,4S,6S)-2-ethyl-2-phenyl-4-(2-piperidyl)-1,3-dioxolane) were prepared and tested for their ability to displace [H-3]TCP (1-[1-(2-thienyl)cyclohexyl]piperidine) from PCP (1-(1-phenylcyclohexyl)piperidine) binding sites in rat brain tissue homogenates. Qualitative structure-activity relationships within this series were explored through modifications of the three major structural units of dexoxadrol, the piperidine, 1,3-dioxolane, and aromatic rings of the molecule. N-Alkyl derivatives of dexoxadrol were found to be inactive, as were those analogues where the dioxolane ring was modified. Phenyl-substituted etoxadrol analogues were compared to similarly substituted PCP analogues and distinct differences were found in their structure-activity relationships suggesting that the aromatic rings in these two drug classes interact differently with the PCP binding sites. The replacement of the phenyl ring in etoxadrol by either a 2- or 3-thienyl ring led to compounds with affinity comparable to etoxadrol, and the replacement of the ethyl moiety on etoxadrol's dioxolane ring with propyl (7) or isopropyl (8) led to compounds which were more potent than etoxadrol or PCP. The most potent compound was (2S,4S,6S)-2-ethyl-2-(1-chlorophenyl)-4-(2-piperidyl)-1,3-dioxolane (11), where a chlorine moiety was placed in the ortho position in the aromatic ring of etoxadrol. Its potency was comparable with TCP in vitro.

  DOI：

  10.1021/jm00086a001

文献信息

• Analogs of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure activity relationships
  作者：Andrew Thurkauf、Mariena V. Mattson、Scott Richardson、Seid Mirsadeghi、Paul L. Ornstein、Ernest A. Harrison、Kenner C. Rice、Arthur E. Jacobson、James A. Monn

  DOI：10.1021/jm00086a001

  日期：1992.4

  A series of dioxolane analogues based on dexoxadrol ((4S,6S)-2,2-diphenyl-4-(2-piperidyl)-1,3-dioxolane) and etoxadrol ((2S,4S,6S)-2-ethyl-2-phenyl-4-(2-piperidyl)-1,3-dioxolane) were prepared and tested for their ability to displace [H-3]TCP (1-[1-(2-thienyl)cyclohexyl]piperidine) from PCP (1-(1-phenylcyclohexyl)piperidine) binding sites in rat brain tissue homogenates. Qualitative structure-activity relationships within this series were explored through modifications of the three major structural units of dexoxadrol, the piperidine, 1,3-dioxolane, and aromatic rings of the molecule. N-Alkyl derivatives of dexoxadrol were found to be inactive, as were those analogues where the dioxolane ring was modified. Phenyl-substituted etoxadrol analogues were compared to similarly substituted PCP analogues and distinct differences were found in their structure-activity relationships suggesting that the aromatic rings in these two drug classes interact differently with the PCP binding sites. The replacement of the phenyl ring in etoxadrol by either a 2- or 3-thienyl ring led to compounds with affinity comparable to etoxadrol, and the replacement of the ethyl moiety on etoxadrol's dioxolane ring with propyl (7) or isopropyl (8) led to compounds which were more potent than etoxadrol or PCP. The most potent compound was (2S,4S,6S)-2-ethyl-2-(1-chlorophenyl)-4-(2-piperidyl)-1,3-dioxolane (11), where a chlorine moiety was placed in the ortho position in the aromatic ring of etoxadrol. Its potency was comparable with TCP in vitro.
• Synthesis of tritium and carbon-14 labeled 1, 3-dioxolanes
  作者：Richard S. P. Hsi、Richard C. Thomas

  DOI：10.1002/jlcr.2590090306

  日期：1973.7

  Condensation of dimethoxdipheny Lmethane14C (III) with the levortatory (IIa) and dextrorotatory (IIb) isomers of 2-(2-piperidyl) -1, 2-ethamediol hydrochloride, obtained respectively by hydrolysis from the d and 2 isomers (Ia and Ib) of the lower melting racemate of 2, 2-diphenyl-4-(2-piperidyl)-1, 3-dioxolane hydrochloride, produces the carbon-14 labeled dioxolanee Ic and Id with retention of configruation at the asymetric carbon atoms. Stepwise reduction of 2,2-dipheny 1-4-(1-benzyl-1-2-pyridy 1)-1, 3-dioxolane. The lower melting racemate was isolated as ists di-tartaric acid salt (If) and resolved to give optically active tritium-labeled dixolanes Ig and Ih.

  将二甲氧基二苯甲烷 14C （III）与 2-(2-哌啶基)-1，2-乙二醇盐酸盐的左旋（IIa）和右旋（IIb）异构体缩合、2-二苯基-4-(2-哌啶基)-1, 3-二氧戊环盐酸盐，生成碳-14 标记的二氧戊环 Ic 和 Id，并在非对称碳原子上保留构型。逐步还原 2,2-二苯基 1-4-(1-苄基-1-2-吡啶 1)-1,3-二氧戊环。分离出熔点较低的外消旋体异构体二酒石酸盐（If），并进行解析，得到具有光学活性的氚标记的二氧戊环 Ig 和 Ih。