N-t-butoxycarbonyl-4-hydroxy-2-methyl-4-(6-methylbenzo[b]thiophen-2-yl)piperidine | 346591-72-8

• 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-t-butoxycarbonyl-4-hydroxy-2-methyl-4-(6-methylbenzo[b]thiophen-2-yl)piperidine
• 英文别名: Tert-butyl 4-hydroxy-2-methyl-4-(6-methyl-1-benzothiophen-2-yl)piperidine-1-carboxylate
• CAS: 346591-72-8
• 化学式: C₂₀H₂₇NO₃S
• 分子量: 361.505
• InChiKey: ILBVWIORHUUCGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-t-butoxycarbonyl-4-hydroxy-2-methyl-4-(6-methylbenzo[b]thiophen-2-yl)piperidine 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S)-1-(1H-indol-4-yl)oxy-3-[(2R,4S)-2-methyl-4-(6-methylbenzo[b]thiophen-2-yl)piperidinyl]-2-propanol
  参考文献：
  名称：

  Advances Toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 2

  摘要：

  Potent 5-HT1A/SSRIs at low nanomolar and subnanomolar concentrations were identified in a series of 1-(1H-indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols. Incorporation of an alpha-Me group in the piperidine ring with its specific stereochemistry enhanced binding affinity at the 5-HT reuptake site and in vitro 5-HT1A antagonist functional activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00392-5
• 作为产物：
  描述：

  6-甲基苯并噻吩 、 1-叔丁氧羰基-2-甲基-哌啶酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.67h， 以45%的产率得到N-t-butoxycarbonyl-4-hydroxy-2-methyl-4-(6-methylbenzo[b]thiophen-2-yl)piperidine
  参考文献：
  名称：

  Indole derivatives for the treatment of depression and anxiety

  摘要：

  本发明提供了以下化合物的公式（I）：这些化合物对治疗抑郁症、焦虑症，并缓解因戒烟或部分戒烟引起的症状非常有用。

  公开号：

  US20040006229A1

文献信息

• Indole derivatives for the treatment of depression and anxiety
  申请人：——

  公开号：US20040006229A1

  公开（公告）日：2004-01-08

  The present invention provides compounds of formula (I): which are useful for treating depression, anxiety, and alleviating the symptoms caused by withdrawal or partial withdrawal from the use of tobacco or of nicotine. 1

  本发明提供了以下化合物的公式（I）：这些化合物对治疗抑郁症、焦虑症，并缓解因戒烟或部分戒烟引起的症状非常有用。
• Process for preparing 4-substituted piperidines
  申请人：——

  公开号：US20030153764A1

  公开（公告）日：2003-08-14

  The present invention provides a process for preparing N-protected-4-substituted piperidines of formula (I) wherein Pg represents a suitable nitrogen protecting group; X represents a heterocycle, substituted heterocycle, substituted alkenyl or substituted aryl wherein the substituted heterocycle, substituted alkenyl or substituted aryl are substituted with from 1 to 3 suitable activating groups; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 each independently represent an alkyl, alkenyl, cycloalkyl, aryl, substituted aryl, heterocycle, or substituted heterocycle, comprising treating a compound of formula (II) wherein the substituents are defined as above, with triethylsilane and trifluoroacetic acid.

  本发明提供了一种制备式（I）的 N-保护-4-取代哌啶的工艺 其中 Pg 代表合适的氮保护基团；X 代表杂环、取代的杂环、取代的烯基或取代的芳基， 其中取代的杂环、取代的烯基或取代的芳基被 1 至 3 个合适的活化基团取代；以及 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 和 R 8 各自独立地代表烷基、烯基、环烷基、芳基、取代芳基、杂环或取代杂环，包括用三乙基硅烷和三氟乙酸处理式（II）化合物，其中取代基定义如上。
• INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION AND ANXIETY
  申请人：ELI LILLY AND COMPANY

  公开号：EP1242411B1

  公开（公告）日：2006-03-08
• US7144898B2
  申请人：——

  公开号：US7144898B2

  公开（公告）日：2006-12-05
• Advances Toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 2
  作者：Kumiko Takeuchi、Todd J Kohn、Nicholas A Honigschmidt、Vincent P Rocco、Patrick G Spinazze、Daniel J Koch、Steven T Atkinson、Larry W Hertel、David L Nelson、D.Bradley Wainscott、Laura J Ahmad、Janice Shaw、Penny G Threlkeld、David T Wong

  DOI：10.1016/s0960-894x(03)00392-5

  日期：2003.7

  Potent 5-HT1A/SSRIs at low nanomolar and subnanomolar concentrations were identified in a series of 1-(1H-indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols. Incorporation of an alpha-Me group in the piperidine ring with its specific stereochemistry enhanced binding affinity at the 5-HT reuptake site and in vitro 5-HT1A antagonist functional activity. (C) 2003 Elsevier Science Ltd. All rights reserved.