tert-butyl (2S)-2-[(E)-3-methoxy-3-oxoprop-1-enyl]piperidine-1-carboxylate | 212556-98-4

• 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: tert-butyl (2S)-2-[(E)-3-methoxy-3-oxoprop-1-enyl]piperidine-1-carboxylate
• CAS: 212556-98-4
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: CFXAGYWRABXDSH-FBOQAHMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[(E)-3-methoxy-3-oxoprop-1-enyl]piperidine-1-carboxylate 在 palladium on activated charcoal 二甲基硫 、 硼烷 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (+)-coniceine
  参考文献：
  名称：

  Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

  摘要：

  The kinetic resolutions of both (+/-)-N-(benzyloxycarbonyl-2-(hydroxymethyl)piperidine [(+/-)-5] and (+/-)-N(tert-butoxycarbonyi)-2-(hydroxymethyl)piperidine [(+/-)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)-6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2-4 steps) and proceeded with satisfactory overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00178-5
• 作为产物：
  描述：

  2-哌啶甲醇 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 tert-butyl (2S)-2-[(E)-3-methoxy-3-oxoprop-1-enyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

  摘要：

  The kinetic resolutions of both (+/-)-N-(benzyloxycarbonyl-2-(hydroxymethyl)piperidine [(+/-)-5] and (+/-)-N(tert-butoxycarbonyi)-2-(hydroxymethyl)piperidine [(+/-)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)-6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2-4 steps) and proceeded with satisfactory overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00178-5

文献信息

• NEUROTROPHIC DIAMIDE AND CARBAMATE AGENTS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1129070A1

  公开（公告）日：2001-09-05
• EP1129070A4
  申请人：——

  公开号：EP1129070A4

  公开（公告）日：2005-03-02
• US6228872B1
  申请人：——

  公开号：US6228872B1

  公开（公告）日：2001-05-08
• [EN] NEUROTROPHIC DIAMIDE AND CARBAMATE AGENTS<br/>[FR] AGENTS NEUROTROPHIQUES DE DIAMIDE ET CARBAMATE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2000027811A1

  公开（公告）日：2000-05-18

  The present invention relates to the design, synthesis, and the peptidyl-prolyl isomerase (PPIase or rotamase) inhibitory activity of novel pyrrolidinemethyl diamide and carbamate compounds that are neurotrophic agents (i.e. compounds capable of stimulating growth or proliferation of nervous tissue) and that bind to immunophilins such as FKBP12 and inhibit their rotamase activity. This invention also relates to pharmaceutical compositions comprising these compounds.