benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate | 156782-68-2

• 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: benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate
• CAS: 156782-68-2
• 化学式: C₁₉H₂₀FNO₃
• 分子量: 329.371
• InChiKey: BDUMKHLUSMCQJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate 在 四氧化锇 N-甲基吲哚酮 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.25h， 生成 Benzyl 4-(4-fluorophenyl)-3,4-dihydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

  摘要：

  A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.015
• 作为产物：
  描述：

  4-羟基-1-哌啶甲酸苄酯 在 jones reagent 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 2.25h， 生成 benzyl 4-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

  摘要：

  A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.015

文献信息

• Catalytic Friedel‐Crafts Reactions on Saturated Heterocycles and Small Rings for sp ³ ‐sp ² Coupling of Medicinally Relevant Fragments
  作者：Rosemary A. Croft、Maryne A. J. Dubois、Alexander J. Boddy、Camille Denis、Anna Lazaridou、Anne Sophie Voisin‐Chiret、Ronan Bureau、Chulho Choi、James J. Mousseau、James A. Bull

  DOI：10.1002/ejoc.201900498

  日期：2019.9

  A systematic comparison of Lewis acid catalysts [Ca(II), Li(I) and Fe(III)] is presented for catalytic Friedel–Crafts reactions using alcohols on 4‐, 5‐, and 6‐membered oxygen and nitrogen heterocycles and cyclobutanes, forming gem‐diaryl quaternary centers.

  路易斯酸催化剂[Ca（II），Li（I）和Fe（III）]的系统比较被提出用于使用醇在4、5和6元氧和氮杂环和环丁烷上进行的催化Friedel-Crafts反应，形成宝石-二芳基四元中心。
• NEUROPROTECTIVE 3,4-DIHYDRO-2(1H)-QUINOLONE COMPOUNDS
  申请人：PFIZER INC.

  公开号：EP0666854A1

  公开（公告）日：1995-08-16
• US5852040A
  申请人：——

  公开号：US5852040A

  公开（公告）日：1998-12-22
• [EN] NEUROPROTECTIVE 3,4-DIHYDRO-2(1H)-QUINOLONE COMPOUNDS<br/>[FR] COMPOSES NEUROPROTECTEURS DE 3,4-DIHYDRO-2(1H)-QUINOLONE
  申请人：PFIZER INC.

  公开号：WO1994010166A1

  公开（公告）日：1994-05-11

  (EN) The present invention is directed to compounds of formula (I), and the pharmaceutically acceptable acid addition salts thereof, wherein R is selectetd from the group consisting of F, -CF3, -OCH3, -O(C1)alkyl substituted with 1 to 3 fluoro atoms, -O(C2)alkyl substituted with 1 to 5 fluoro atoms, and -O(C3)alkyl substituted with 1 to 7 fluoro atoms. The compounds of formula (I) are useful in the treatment of stroke, traumatic brain injury and central nervous system degenerative diseases.(FR) La présente invention se rapporte à des composés de la formule (I) et à des sels d'addition d'acide pharmaceutiquement acceptables de ceux-ci. Dans ladite formule R est sélectionné dans le groupe constitué de F, -CF3, -OCH3, -O(C1)alkyle substitué avec 1 à 3 atomes fluorés, -O(C2)alkyle remplacé par 1 à 5 atomes fluoro, et -O(C3)alkyle remplacé par 1 à 7 atomes fluoro. Les composés de la formule (I) sont utiles dans le traitement de l'ictus cérébral, de lésions cérébrales traumatiques et de maladies dégénératives du système nerveux central.
• Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline
  作者：Meng-Yang Chang、Chun-Li Pai、Yung-Hua Kung

  DOI：10.1016/j.tetlet.2005.10.015

  日期：2005.12

  A straightforward synthesis of (+/-)-coerulescine and (+/-)-horsfiline has been established from 3-formyl-3-phenylpyrridine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (+/-)-coerulescine and ()-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3-plienylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton. (c) 2005 Elsevier Ltd. All rights reserved.