1-tert-butyl 3-(pyridine-2-yl)azetidine-1-carboxylate | 206446-39-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 1-tert-butyl 3-(pyridine-2-yl)azetidine-1-carboxylate
• 英文别名: 2(N-tert-butoxycarbonylazetidinyl)pyridine；tert-butyl 3-pyridin-2-ylazetidine-1-carboxylate；Tert-butyl 3-(pyridin-2-yl)azetidine-1-carboxylate
• CAS: 206446-39-1
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: WOZILFWABRXAFR-UHFFFAOYSA-N

物化性质

• 沸点：
  343.9±35.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 3-(pyridine-2-yl)azetidine-1-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 2-(azetidin-3-yl)pyridine dihydrochloride
  参考文献：
  名称：

  Synthesis of C-Substituted Cyclic Amines Using Azacycloalkyl Organozinc Reagents

  摘要：

  由相应的氮杂环烷基碘化物通过直接锌插入法制备了来源于氮杂环丁烷和哌啶的有机锌物种。研究表明，它们能够顺利进行Pd(0)介导的交叉偶联反应，并与CuCN·2LiCl发生转金属反应。

  DOI：

  10.1055/s-1998-37503
• 作为产物：
  描述：

  1-Boc-3-碘氮杂环丁烷 在 四(三苯基膦)钯 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 1,2-二溴乙烷 为溶剂， 反应 2.67h， 生成 1-tert-butyl 3-(pyridine-2-yl)azetidine-1-carboxylate
  参考文献：
  名称：

  抗肿瘤杂环药物中间体2-(3-氮杂环丁基）吡啶二盐酸盐的合成方法

  摘要：

  本发明公开了抗肿瘤杂环药物中间体2‑(3‑氮杂环丁基)吡啶二盐酸盐的合成方法，具体为以3‑碘‑1‑叔丁氧羰基氮杂环丁烷和2‑溴吡啶原料，经过两步反应得到目标化合物2‑(3‑氮杂环丁基)吡啶类二盐酸盐。本发明使用的原料简单、成本低廉、容易得到，且反应条件简单、得到的产品化学纯度高。

  公开号：

  CN106957300A

文献信息

• AMINO-HETEROCYCLIC COMPOUNDS
  申请人：Claffey Michelle M.

  公开号：US20100190771A1

  公开（公告）日：2010-07-29

  The invention provides PDE9-inhibiting compounds of Formula (I), and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , A, and n are as defined herein. Pharmaceutical compositions containing the compounds of Formula I, and uses thereof in treating neurodegenerative and cognitive disorders, such as Alzheimer's disease and schizophrenia, are also provided.

  这项发明提供了式（I）中的PDE9抑制化合物，以及其药学上可接受的盐，其中R1、R2、R3、A和n的定义如本文所述。还提供了含有式I中化合物的药物组合物，并且提供了在治疗神经退行性和认知障碍疾病，如阿尔茨海默病和精神分裂症中的用途。
• Amino-Heterocyclic Compounds
  申请人：Claffey Michelle Marie

  公开号：US20120329777A1

  公开（公告）日：2012-12-27

  The invention provides PDE9-inhibiting compounds of Formula (I), and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , A, and n are as defined herein. Pharmaceutical compositions containing the compounds of Formula I, and uses thereof in treating neurodegenerative and cognitive disorders, such as Alzheimer's disease and schizophrenia, are also provided.

  本发明提供了PDE9抑制化合物(I)及其药学上可接受的盐，其中R1、R2、R3、A和n如本文所定义。还提供了含有化合物I的药物组合物，并将其用于治疗神经退行性和认知障碍，如阿尔茨海默病和精神分裂症。
• Continuous Synthesis of Organozinc Halides Coupled to Negishi Reactions
  作者：Nerea Alonso、L. Zane Miller、Juan de M. Muñoz、Jesus Alcázar、D. Tyler McQuade

  DOI：10.1002/adsc.201400243

  日期：2014.12.15

  AbstractThe Negishi cross‐coupling is a powerful CC bond forming reaction. The method is less commonly used relative to other cross‐coupling methods in part due to lack of availability of organozinc species. While organozinc species can be prepared, problems with reproducibility and handling of these sensitive species can complicate these reactions. Herein, we describe the continuous formation, using an activated packed‐bed of metallic zinc, and subsequent use of organozinc halides. We demonstrate that a single column of zinc can provide excellent yields of organozinc halides and that they can be used downstream in subsequent Negishi cross‐couplings. The preparation of the zinc column and the scope of the reaction are discussed.magnified image
• Discovery of azetidine based ene-amides as potent bacterial enoyl ACP reductase (FabI) inhibitors
  作者：Mohamed Takhi、Kandepu Sreenivas、Chandrashekar K. Reddy、Mahadari Munikumar、Kolakota Praveena、Pabolu Sudheer、Bandaru N.V.M. Rao、Gollamudi Ramakanth、Jampala Sivaranjani、Shardaprasad Mulik、Yeruva R. Reddy、Krishnamurthy Narasimha Rao、Rentala Pallavi、Anirudha Lakshminarasimhan、Sunil K. Panigrahi、Thomas Antony、Iskandar Abdullah、Yean K. Lee、Murali Ramachandra、Rohana Yusof、Noorsaadah A. Rahman、Hosahalli Subramanya

  DOI：10.1016/j.ejmech.2014.07.036

  日期：2014.9

  A novel and potent series of ene-amides featuring azetidines has been developed as FabI inhibitors active against drug resistant Gram-positive pathogens particularly staphylococcal organisms. Most of the compounds from the series possessed excellent biochemical inhibition of Staphylococcus aureus FabI enzyme and whole cell activity against clinically relevant MRSA, MSSA and MRSE organisms which are responsible for significant morbidity and mortality in community as well as hospital settings. The binding mode of one of the leads, AEA16, in Escherichia coli FabI enzyme was determined unambiguously using X-ray crystallography. The lead compounds displayed good metabolic stability in mice liver microsomes and pharmacokinetic profile in mice. The in vivo efficacy of lead AEA16 has been demonstrated in a lethal murine systemic infection model.
• Amino-heterocyclic compounds used as pde9 inhibitors
  申请人：Pfizer Inc.

  公开号：EP2389382B1

  公开（公告）日：2013-06-05