ethyl (3R)-3-(dimethylamino)pyrrolidine-1-carboxylate | 1246299-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ethyl (3R)-3-(dimethylamino)pyrrolidine-1-carboxylate
• CAS: 1246299-44-4
• 化学式: C₉H₁₈N₂O₂
• 分子量: 186.254
• InChiKey: IWTPHODZCHYRTD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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 (3R)-3-(dimethylamino)pyrrolidine-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以90%的产率得到dimethyl-((R)-1-methylpyrrolidin-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：

  (R)-(+)-3-(dimethylamino)pyrrolidine 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100%的产率得到ethyl (3R)-3-(dimethylamino)pyrrolidine-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

• [EN] HPK1 INHIBITOR, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] INHIBITEUR DE HPK1, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] HPK1抑制剂及其制备方法和用途
  申请人：WIGEN BIOMEDICINE TECH SHANGHAI CO LTD

  公开号：WO2021213317A1

  公开（公告）日：2021-10-28

  本发明涉及一种通式(1)所示的化合物及其制备方法，及如通式(1)所示的化合物或其各异构体、各晶型、药学上可接受的盐、水合物或溶剂合物作为HPK1抑制剂的用途。本发明化合物可用于制备治疗或者预防由HPK1介导的相关疾病。
• 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.