Ethyl 3-(dimethylamino)piperidine-1-carboxylate | 1071033-72-1

• 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: Ethyl 3-(dimethylamino)piperidine-1-carboxylate
• CAS: 1071033-72-1
• 化学式: C₁₀H₂₀N₂O₂
• 分子量: 200.281
• InChiKey: KCUGUNLUKRGODF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(dimethylamino)piperidine-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以58%的产率得到dimethyl-(1-methylpiperidin-3-yl)amine
  参考文献：
  名称：

  Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry

  摘要：

  Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.038
• 作为产物：
  描述：

  3-dimethylaminopiperidine dihydrochloride 、 氯甲酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到Ethyl 3-(dimethylamino)piperidine-1-carboxylate
  参考文献：
  名称：

  Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry

  摘要：

  Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.038

文献信息

• Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry
  作者：Mickael Pouliquen、Jérôme Blanchet、Michaël De Paolis、B. Rema Devi、Jacques Rouden、Marie-Claire Lasne、Jacques Maddaluno

  DOI：10.1016/j.tetasy.2010.04.038

  日期：2010.6

  Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee. (C) 2010 Elsevier Ltd. All rights reserved.