N-acetyl-3-carboxymethylpiperidine | 111479-16-4

• 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: N-acetyl-3-carboxymethylpiperidine
• 英文别名: N-acetyl-piperidine-3-carboxylic acid methyl ester；1-Acetyl-piperidine-3-carboxylic acid methyl ester；methyl 1-acetylpiperidine-3-carboxylate
• CAS: 111479-16-4
• 化学式: C₉H₁₅NO₃
• mdl: MFCD16293355
• 分子量: 185.223
• InChiKey: OWSGPYSADALYKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-acetyl-3-carboxymethylpiperidine 以82%的产率得到
  参考文献：
  名称：

  TOONE, ERIC J.;JONES, J. BRYAN, CAN. J. CHEM., 65,(1987) N 12, 2722-2726

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶-3-羧酸盐酸盐 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 27.0h， 生成 N-acetyl-3-carboxymethylpiperidine
  参考文献：
  名称：

  Chemoenzymatic approach to enantiopure piperidine-based β-amino esters in organic solvents

  摘要：

  This research concentrates on the enantioselectivities of lipase-catalysed reactions with methyl esters of 2-piperidylacetic acid and 3-piperidinecarboxylic acid derivatives. N-Acetylated 2-piperidylacetic acid methyl ester displayed good enantioselectivity (E = 66) in a 1:1 mixture of diisopropyl ether and butyl butanoate in the presence of lipase PS-C IT from Burkholderia cepacia. The reaction is known as interesterification with butyl butanoate rather than alcoholysis with the butanol, because butyl butanoate has to be first hydrolysed or go through alcoholysis with MeOH in order to release butanol. Other N-protective groups (Boc, Ns, Fmoc and Bzn) gave excellent en anti oselectivity (E > 200) under the same conditions, and a gram-scale resolution was performed with N-Boc-2-piperidylacetic acid methyl ester. Reaction with a 3-piperidylcarboxylic acid derivative took place with disappointingly low enantioselectivity (E = 4), with Candida antarctica lipase B being the best of the lipases screened. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.027

文献信息

• Enzymes in organic synthesis. 40. Evaluation of the enantioselectivity of the pig liver esterase catalyzed hydrolyses of racemic piperidine carboxylic acid esters
  作者：Eric J. Toone、J. Bryan Jones

  DOI：10.1139/v87-452

  日期：1987.12.1

  Pig liver esterase (PLE) catalyzed hydrolysis of racemic piperidine esters proceeds enantioselectively to give product acids and recovered esters in 0–47% enantiomeric excess.

  猪肝酯酶 (PLE) 催化的外消旋哌啶酯水解以对映选择性进行，以产生 0-47% 对映体过量的产物酸和回收酯。
• TOONE, ERIC J.;JONES, J. BRYAN, CAN. J. CHEM., 65,(1987) N 12, 2722-2726
  作者：TOONE, ERIC J.、JONES, J. BRYAN

  DOI：——

  日期：——
• Chemoenzymatic approach to enantiopure piperidine-based β-amino esters in organic solvents
  作者：Arto Liljeblad、Hanna-Maija Kavenius、Petri Tähtinen、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2007.01.027

  日期：2007.2

  This research concentrates on the enantioselectivities of lipase-catalysed reactions with methyl esters of 2-piperidylacetic acid and 3-piperidinecarboxylic acid derivatives. N-Acetylated 2-piperidylacetic acid methyl ester displayed good enantioselectivity (E = 66) in a 1:1 mixture of diisopropyl ether and butyl butanoate in the presence of lipase PS-C IT from Burkholderia cepacia. The reaction is known as interesterification with butyl butanoate rather than alcoholysis with the butanol, because butyl butanoate has to be first hydrolysed or go through alcoholysis with MeOH in order to release butanol. Other N-protective groups (Boc, Ns, Fmoc and Bzn) gave excellent en anti oselectivity (E > 200) under the same conditions, and a gram-scale resolution was performed with N-Boc-2-piperidylacetic acid methyl ester. Reaction with a 3-piperidylcarboxylic acid derivative took place with disappointingly low enantioselectivity (E = 4), with Candida antarctica lipase B being the best of the lipases screened. (c) 2007 Elsevier Ltd. All rights reserved.