4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydropyridine | 100332-09-0

• 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: 4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydropyridine
• 英文别名: (+/-)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,6-tetrahydropyridine；4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,6-tetrahydropyridine；[4-(4-fluorophenyl)-1-methyl-3,6-dihydro-2H-pyridin-3-yl]methanol
• CAS: 100332-09-0；100332-10-3；100332-14-7
• 化学式: C₁₃H₁₆FNO
• 分子量: 221.275
• InChiKey: MXIFCNZZUPFATE-UHFFFAOYSA-N

物化性质

• 沸点：
  315.4±42.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydropyridine 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 溴化氰 、 氢气 、 sodium 、 三乙胺 、 苯磺酰氯 作用下， 反应 76.0h， 生成 (+)-cis-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine hydrochloride
  参考文献：
  名称：

  Synthesis and 5HT Modulating Activity of Stereoisomers of 3-Phenoxymethyl-4-phenylpiperidines.

  摘要：

  A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or alpha-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT(2A) and 5HT(2C) receptors.

  DOI：

  10.3891/acta.chem.scand.50-0164
• 作为产物：
  描述：

  帕罗西汀USPRCE 、 盐酸 、 聚合甲醛 、 氨 在 甲苯 作用下， 以 硫酸 、 水 为溶剂， 反应 5.0h， 以gave 38 g of 4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,6-tetrahydropyridine with b.p. 110°-120° C at 0.1 mm Hg的产率得到4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  4-Phenylpiperidine compounds

  摘要：

  该发明涉及新的3-取代的1-烷基-4-苯基哌啶衍生物，可用作抗抑郁和抗帕金森病药物，并涉及其制备方法。

  公开号：

  US04007196A1

文献信息

• Novel process
  申请人：SmithKline Beecham p.l.c.

  公开号：US20020010155A1

  公开（公告）日：2002-01-24

  A process for the preparation of a 4-aryl-3-oxymethyl-piperidine of structure (1) 1 in which R is hydrogen or an alkyl, arylalkyl, allyl, acyl, carbonyloxyalkyl, carbonyloxyaryl, or carbonyloxyalkylaryl group, and Y is a hydrogen atom or an optionally substituted alkyl, arylalkyl, or aryl group, from a carboxy derivative of structure (2) 2 where A is oxygen or sulphar, X is one or more of hydrogen, or a readily reducible group, Z represents either a hydrogen atom or an OY′ group in which Y′ is independently selected from the same groups as Y, and the broken line circle indicates bonding, appropriate to a tetrahydropyridine, dihydropyridine, pyridine, or piperidine ring said process comprising (a) when Y is a hydrogen atom, reducing the compound of structure (2), or (b) when Y is other than a hydrogen atom (i) forming an ether from the alcohol product of step (a), (ii) etherifying the aldehyde compound of structure (2) in which Z is hydrogen, or (iii) reducing the ester compound of structure (2) in which Z is OY′.

  一种制备结构（1）中的4-芳基-3-氧甲基-哌啶的方法，其中R是氢或烷基、芳基烷基、烯丙基、酰基、羰基氧烷基、羰基氧芳基或羰基氧烷基芳基，Y是氢原子或可选择取代的烷基、芳基烷基或芳基，从结构（2）中的羧衍生物进行，其中A是氧或硫，X是一个或多个氢或易还原基团，Z代表氢原子或OY′基团，其中Y′独立选择自Y相同的基团，中断线圆表示键合，适用于四氢吡啶、二氢吡啶、吡啶或哌啶环的过程包括(a)当Y是氢原子时，还原结构（2）的化合物，或(b)当Y不是氢原子时(i)从步骤（a）的醇产物中形成醚，(ii)使结构（2）中Z为氢的醛化合物醚化，或(iii)还原结构（2）中Z为OY′的酯化合物。
• A phenylpiperidine derivative, and its salts, their preparation, compositions containing them, and their therapeutic use
  申请人：A/S FERROSAN

  公开号：EP0152273A2

  公开（公告）日：1985-08-21

  (-)-trans-4-(4-Fluorophenyl)-3-(4-methoxyphenoxy)-methyl]piperidine and its acid addition salts are novel compounds of utility in potentiating serotonin. They are prepared by demethylating the corresponding 1-methylpiperidine.

  (-)-反式-4-(4-氟苯基)-3-(4-甲氧基苯氧基)-甲基]哌啶及其酸加成盐是一种新型化合物，可用于增效血清素。它们是通过对相应的 1-甲基哌啶进行去甲基化而制备的。
• Piperidine derivatives having a gastro-intestinal activity
  申请人：BEECHAM GROUP PLC

  公开号：EP0190496A2

  公开（公告）日：1986-08-13

  Compounds of formula (I) and pharmaceutically acceptable salts thereof: wherein R, and R2 are both hydrogen or together are a bond; R3 and R4 are independently optionally substituted phenyl or naphthyl groups; Rs is a group (CH2)nR6 wherein n is 1 or 2 and R6 is an optionally substituted phenyl or naphthyl group having activity against disorders relating to impaired gastro-intestinal motility, a process and intermediates for their preparation and their use as pharmaceuticals

  式(I)化合物及其药学上可接受的盐： 其中R和R2均为氢或共为键；R3和R4独立地为任选取代的苯基或萘基；Rs为基团(CH2)nR6，其中n为1或2，R6为任选取代的苯基或萘基，对胃肠道运动障碍相关疾病具有活性，制备它们的工艺和中间体以及它们作为药物的用途
• LASSEN, J. B.;CHRISTENSEN, J. A.;PETERSEN, E. N.;HANSEN, J. B.
  作者：LASSEN, J. B.、CHRISTENSEN, J. A.、PETERSEN, E. N.、HANSEN, J. B.

  DOI：——

  日期：——
• PROCESS FOR THE RACEMISATION OF 1-BENZYL-4-(4-FLUOROPHENYL)-3-HYDROXYMETHYL-1,2,3,6-TETRAHYDROPYRIDINE TO BE USED AS INTERMEDIATE IN THE SYNTHESIS OF PAROXETINE
  申请人：Aesica Pharmaceuticals Ltd.

  公开号：EP1315701B1

  公开（公告）日：2009-01-28