Piperidine-1-carboxylic acid prop-2-ynyl ester | 123477-58-7

• 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: Piperidine-1-carboxylic acid prop-2-ynyl ester
• 英文别名: Prop-2-ynyl piperidine-1-carboxylate
• CAS: 123477-58-7
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: GDMFMEIHLSAJSY-UHFFFAOYSA-N

物化性质

• 沸点：
  239.3±23.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Piperidine-1-carboxylic acid prop-2-ynyl ester 在 benzyltriethylammonium tetrathiomolybdate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以96%的产率得到哌啶
  参考文献：
  名称：

  A mild and selective method for N-dealkylation of tertiary amines

  摘要：

  Alkyl groups can be cleaved efficiently and selectively from tertiary alkyl amines using propargyl chloroformate. The propargyloxycarbonyl (Poc) protected secondary amines thus obtained can be deblocked under neutral and mild conditions using benzyltriethylammonium tetrathiomolybdate. The generality and compatibility of the method have been studied with a wide range of functionalities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.018
• 作为产物：
  描述：

  N-甲基哌啶 、 炔丙基氯甲酸酯 以 氯仿 为溶剂， 反应 1.5h， 以51%的产率得到Piperidine-1-carboxylic acid prop-2-ynyl ester
  参考文献：
  名称：

  A mild and selective method for N-dealkylation of tertiary amines

  摘要：

  Alkyl groups can be cleaved efficiently and selectively from tertiary alkyl amines using propargyl chloroformate. The propargyloxycarbonyl (Poc) protected secondary amines thus obtained can be deblocked under neutral and mild conditions using benzyltriethylammonium tetrathiomolybdate. The generality and compatibility of the method have been studied with a wide range of functionalities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.018

文献信息

• Synthesis of Tertiary Amines through Extrusive Alkylation of Carbamates
  作者：Guoliang Zhang、David Favela、Winston L. Chow、Rishab N. Iyer、Alexander J. Pell、David E. Olson

  DOI：10.1021/acs.orglett.2c02516

  日期：2022.8.26

  Basic amines are key elements of many biologically active natural products and pharmaceuticals. Given their inherent reactivity, it is often necessary to protect basic amines during target-directed synthesis, which results in wasteful protection/deprotection sequences. We report a step-economical approach enabling the protection of secondary amines as carbamates prior to their conversion to tertiary

  碱性胺是许多具有生物活性的天然产物和药物的关键元素。鉴于其固有的反应性，在靶向合成过程中通常需要保护碱性胺，这会导致保护/脱保护序列的浪费。我们报告了一种分步经济的方法，能够在仲胺通过 CO 2的正式挤出转化为叔胺之前将其保护为氨基甲酸酯。该方法适用于 iboga 生物碱 (±)-conodusine A 和 (±)-conodusine B 的合成。
• SUZUKI, KUNIO;USHIJIMA, RYOSUKE;MIYANO, TETSUJI;NAKAGAWA, SUSUMU, HETEROCYCLES, 29,(1989) N, C. 497-509
  作者：SUZUKI, KUNIO、USHIJIMA, RYOSUKE、MIYANO, TETSUJI、NAKAGAWA, SUSUMU

  DOI：——

  日期：——
• NON-AQUEOUS ELECTROLYTE SOLUTION ADDITIVE, NON-AQUEOUS ELECTROLYTE SOLUTION FOR LITHIUM SECONDARY BATTERY AND LITHIUM SECONDARY BATTERY COMPRISING SAID ADDITIVE
  申请人：LG Chem, Ltd.

  公开号：EP3518334B1

  公开（公告）日：2021-04-21