2-azido-1-(4-(pyrrolidin-1-yl)phenyl)ethanone | 914090-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-1-(4-(pyrrolidin-1-yl)phenyl)ethanone
• 英文别名: 2-azido-1-(4-(pyrrolidine)phenyl)ethanone；2-Azido-1-(4-pyrrolidin-1-ylphenyl)ethanone；2-azido-1-(4-pyrrolidin-1-ylphenyl)ethanone
• CAS: 914090-96-3
• 化学式: C₁₂H₁₄N₄O
• 分子量: 230.269
• InChiKey: GWIKZSFIVWHUCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-1-(4-(pyrrolidin-1-yl)phenyl)ethanone 、 1-benzyl-2-(phenylethynyl)indole-3-carboxaldehyde 在 哌啶乙酸盐 作用下， 以 乙醇 为溶剂， 以80%的产率得到(16-Benzyl-3-phenyl-4,5,6,16-tetrazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),2,4,7,10,12,14-heptaen-7-yl)-(4-pyrrolidin-1-ylphenyl)methanone
  参考文献：
  名称：

  Rapid Access to Novel 1,2,3-Triazolo-Heterocyclic Scaffolds via Tandem Knoevenagel Condensation/Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction in One Pot

  摘要：

  An operationally simple, one-pot, two-step cascade method has been developed to afford biologically important fused 1,2,3-triazolo-heterocyclic scaffolds from 2-alkynyl aryl(heteroaryl) aldehydes and phenacyl azides. This unique atom economical transformation engages four reactive centers (aldehyde, alkyne, active methylene, and azide) under metal-free catalysis.

  DOI：

  10.1021/co500070e
• 作为产物：
  描述：

  1-(4-ethynylphenyl)pyrrolidine 在 dipotassium peroxodisulfate 、 叠氮基三甲基硅烷 、 氧气 、 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以81%的产率得到2-azido-1-(4-(pyrrolidin-1-yl)phenyl)ethanone
  参考文献：
  名称：

  一种α-叠氮羰基化合物及制备方法

  摘要：

  本发明涉及一种α‑叠氮羰基化合物及制备方法，在有机溶剂中，以末端炔烃与三甲基硅叠氮为反应原料，在铜催化剂和过硫酸盐氧化剂的共同促进作用下，通过炔烃的双官能团化反应得到α‑叠氮羰基化合物。叠氮自由基的氧化使用空气作为终端氧化剂在反应过程中起到关键作用。所述方法底物范围广泛、室温操作、反应条件温和、后处理简单以及产物的产率和纯度高，为α‑叠氮羰基类化合物开拓了新的合成路线和方法，具有良好的应用潜力和研究价值。

  公开号：

  CN107056648A

文献信息

• Antagonists of the vanilloid receptor subtype 1 (VR1) and use thereof
  申请人：Gomtsyan Arthur

  公开号：US20060281799A1

  公开（公告）日：2006-12-14

  The present invention is directed to compounds of formula (I) wherein variables W, X, Y, D, A, n, R 1 , R 2 and R 9 are as defined in the description.

  本发明涉及式(I)的化合物，其中变量W、X、Y、D、A、n、R1、R2和R9如描述中所定义。
• ANTAGONISTS OF THE VANILLOID RECEPTOR SUBTYPE 1 (VR1) AND USE THEREOF
  申请人：Gomtsyan Arthur

  公开号：US20100010055A1

  公开（公告）日：2010-01-14

  The present invention is directed to compounds of formula (I) wherein variables W, X, Y, D, A, n, R 1 , R 2 and R 9 are as defined in the description.

  本发明涉及式（I）的化合物，其中变量W，X，Y，D，A，n，R1，R2和R9如描述中所定义。
• Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists
  作者：Richard J. Perner、John R. Koenig、Stanley DiDomenico、Arthur Gomtsyan、Robert G. Schmidt、Chih-Hung Lee、Margaret C. Hsu、Heath A. McDonald、Donna M. Gauvin、Shailen Joshi、Teresa M. Turner、Regina M. Reilly、Philip R. Kym、Michael E. Kort

  DOI：10.1016/j.bmc.2010.04.099

  日期：2010.7

  The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the tetrahydronaphthyl moiety on the 2-amino substituent of the oxazole ring was important for obtaining excellent in vitro potency at the human TRPV1 receptor, while a variety of alkyl and phenyl substituents at the 4- and 5-positions of the oxazole ring were well tolerated and yielded potent TRPV1 antagonists. Despite excellent in vitro potency, the 5-monosubstituted compounds suffered from poor pharmacokinetics. It was found that 4,5-disubstitution on the oxazole ring was critical to the improvement of the overall pharmacokinetic profile of these analogues, which led to the discovery of compound (R)-27, a novel TRPV1 antagonist with good oral activity in preclinical animal models of pain. (C) 2010 Elsevier Ltd. All rights reserved.
• ANTAGONISTS OF THE VANILLOID RECEPTOR SUBTYPE 1 (VR1) AND USES THEREOF
  申请人：ABBOTT LABORATORIES

  公开号：EP1885704A2

  公开（公告）日：2008-02-13
• US7504520B2
  申请人：——

  公开号：US7504520B2

  公开（公告）日：2009-03-17