(+/-)-N-(2-hydroxybutyl)-4-phenylpiperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+/-)-N-(2-hydroxybutyl)-4-phenylpiperidine
• 英文别名: 1-(4-Phenyl-piperidin-1-yl)-butan-2-ol；1-(4-phenylpiperidin-1-yl)butan-2-ol
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: CZOVPNVTVNILDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (+/-)-N-(2-hydroxybutyl)-4-phenylpiperidine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 24.0h， 以69%的产率得到(+/-)-N-(2-acetoxybutyl)-N-methyl-4-phenylpiperidine hydrochloride
  参考文献：
  名称：

  Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)

  摘要：

  Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)-cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography. The absolute configuration of (-)-vesamicol is 1R,2R. Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue. Alterations to all three rings can have large effects on potency. Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.

  DOI：

  10.1021/jm00126a013

文献信息

• 4-Phenyl-2-hydroxybutyl piperidines or morpholines as fungicides
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0129321A2

  公开（公告）日：1984-12-27

  Compounds of formula: and stereoisomers thereof, wherein R', R2, R3, and R4 each represent a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, X and Y each represent a hydrogen or a halogen atom, or an alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, alkoxy, or aryloxy group, Z represents a methylene group or an oxygen atom; and ester and ether derivatives of the alcohol function; and their acid addition salts; have fungicidal activity.

  式化合物及其立体异构体，其中 R'、R2、R3 和 R4 分别代表氢原子或含有 1 至 4 个碳原子的烷基，X 和 Y 分别代表氢原子或卤素原子或烷基、环烷基、烯基、炔基、芳基、芳烷基、烷氧基或芳氧基，Z 代表亚甲基或氧原子；以及醇官能团的酯和醚衍生物；及其酸加成盐；具有杀菌活性。