(S)-2-(2-Methoxycarbonyl-ethyl)-piperidine-1-carboxylic acid t-butyl ester | 267888-42-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (S)-2-(2-Methoxycarbonyl-ethyl)-piperidine-1-carboxylic acid t-butyl ester
• 英文别名: tert-butyl (2S)-2-(3-methoxy-3-oxopropyl)piperidine-1-carboxylate
• CAS: 267888-42-6
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: KZOREEKXGWTFQD-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (S)-2-(2-Methoxycarbonyl-ethyl)-piperidine-1-carboxylic acid t-butyl ester 在 盐酸 、 二甲基硫 、 硼烷 、 sodium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 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：

  (S)-2-甲酰基-1-哌啶甲酸叔丁酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-2-(2-Methoxycarbonyl-ethyl)-piperidine-1-carboxylic acid t-butyl ester
  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：US06228872B1

  公开（公告）日：2001-05-08

  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.

  本发明涉及设计、合成和新型吡咯烷甲基二酰胺和氨基甲酸酯化合物的肽基脯氨酸异构酶（PPIase或旋转酶）抑制活性，这些化合物是神经营养因子（即能够刺激神经组织生长或增殖的化合物），并结合FKBP12等免疫蛋白质抑制其旋转酶活性。本发明还涉及包含这些化合物的制药组合物。
• 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.