benzyl (2R)-2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate | 934422-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2R)-2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate
• CAS: 934422-94-3
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: HFNHPSQNKDZEAM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  benzyl (2R)-2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate 在 lithium aluminium tetrahydride 、 水 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (2R)-N-苄氧羰基-2-(2-羟乙基)哌啶
  参考文献：
  名称：

  [EN] THE R-ISOMER OF 2-{2-[N-(2-INDANYL)-N-PHENYLAMINO]ETHYL}PIPERIDINE AND OTHER DERMAL ANESTHETIC AGENTS
  [FR] R-ISOMERE DE 2-{2-[N-(2-INDANYL)-N-PHENYLAMINO]ETHYL}PIPERIDINE ET AUTRES AGENTS ANESTHESIQUES DERMIQUES

  摘要：

  公开号：

  WO2006037047A3
• 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 、 Burkholderia cepacia PS-C II lipase 、 三乙胺 作用下， 以 氯仿 、 异丙醚 为溶剂， 反应 27.0h， 生成 benzyl (2R)-2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate
  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

• 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.
• [EN] THE R-ISOMER OF 2-{2-[N-(2-INDANYL)-N-PHENYLAMINO]ETHYL}PIPERIDINE AND OTHER DERMAL ANESTHETIC AGENTS<br/>[FR] R-ISOMERE DE 2-{2-[N-(2-INDANYL)-N-PHENYLAMINO]ETHYL}PIPERIDINE ET AUTRES AGENTS ANESTHESIQUES DERMIQUES
  申请人：BRIDGE PHARMA INC

  公开号：WO2006037047A3

  公开（公告）日：2006-09-28