N-acetyl-piperidin-2-yl-acetic acid methyl ester | 111479-15-3

• 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-piperidin-2-yl-acetic acid methyl ester
• 英文别名: methyl 2-(1-acetylpiperidin-2-yl)acetate；N-acetyl-2-carbomethoxymethylpiperidine
• CAS: 111479-15-3
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: CPYAIYARZAMEIE-UHFFFAOYSA-N

物化性质

• 沸点：
  85 °C(Press: 0.1 Torr)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-piperidin-2-yl-acetic acid methyl ester 以100%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：

  2-哌啶乙酸盐酸盐 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-piperidin-2-yl-acetic acid methyl ester
  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。
• An unexpected reaction of pyridine with acetyl chloride to give dihydropyridine and piperidine derivatives
  作者：Pietro Spanu、Alberto Mannu、Fausta Ulgheri

  DOI：10.1016/j.tetlet.2014.02.006

  日期：2014.3

  An unexpected reaction of pyridine with acetyl chloride to give N-acetyl-1,2 and 1,4-dihydropyridyl acetic acid (1, 2) in high yield and regioselectivity has been reported. The key step is the formation of a zwitterionic pyridinium ketene enolate. The effect of different activating agents on the reaction yield and selectivity has been studied. Platinum(IV) mediated hydrogenation of the corresponding

  的意想不到的反应吡啶与乙酰氯，得到ñ -乙酰基-1,2-和1,4-二氢吡啶基乙酸（1，2以高收率和区域选择性）已被报道。关键步骤是两性离子吡啶酮乙烯酮烯醇盐的形成。研究了不同活化剂对反应产率和选择性的影响。铂（IV）相应的甲基酯（介导的氢化7，8），得到哌啶衍生物（9，10）。
• PIPERIDINE COMPOUNDS FOR USE AS OREXIN RECEPTOR ANTAGONIST
  申请人：CHAN Wai Ngor

  公开号：US20090082390A1

  公开（公告）日：2009-03-26

  This invention relates to N-aroyl cyclic amine derivatives and their use as pharmaceuticals, specifically as orexin receptor antagonists.

  本发明涉及N-酰基环状胺衍生物及其作为药物的用途，具体作为促进睡眠的药物，即促进睡眠的药物受体拮抗剂。
• US7423052B2
  申请人：——

  公开号：US7423052B2

  公开（公告）日：2008-09-09
• US7943645B2
  申请人：——

  公开号：US7943645B2

  公开（公告）日：2011-05-17