methyl 2-(4-bromo-N-cyanoanilino)acetate | 1345028-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(4-bromo-N-cyanoanilino)acetate
• CAS: 1345028-90-1
• 化学式: C₁₀H₉BrN₂O₂
• 分子量: 269.098
• InChiKey: FSSFSKTXLODGFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-bromo-N-cyanoanilino)acetate 在 磷酸二丁酯 作用下， 反应 2.0h， 以86%的产率得到1-(4-Bromophenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  在无溶剂条件下高效磷酸二烷基酯介导的乙内酰脲和双环乙内酰脲的合成

  摘要：

  已经通过新策略从基于氰酰胺的前体，即N-氰基-N-烷基/芳基氨基乙酸甲酯合成了不同取代的乙内酰脲。磷酸二烷基酯用作温和的试剂，可在一个步骤中水解和环化底物，以定量获得所需产物。多价乙内酰脲即双乙内酰脲，双环乙内酰脲的合成潜在地扩大了本方法的范围和适用性。无溶剂条件和非常简单的后处理程序使反应变得方便且环保。还报道了一些代表性化合物的单晶结构。

  DOI：

  10.1016/j.tetlet.2011.09.029
• 作为产物：
  描述：

  4-溴苯胺 在 sodium acetate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-(4-bromo-N-cyanoanilino)acetate
  参考文献：
  名称：

  The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties

  摘要：

  The sodium glucose co-transporter 2 (SGLT2) has received considerable attention in recent years as a target for the treatment of type 2 diabetes mellitus. This report describes the design, synthesis and structure-activity relationship (SAR) of C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties as novel SGLT2 inhibitors. Compounds 5p and 33b demonstrated high potency in inhibiting SGLT2 and high selectivity against SGLT1. The in vitro ADMET properties of these compounds will also be discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.036

文献信息

• Novel and efficient protocol for the syntheses of N-1 substituted thiohydantoin and a bicyclothiohydantoin under solvent-free conditions
  作者：Vinod Kumar、Hemlata Rana、Ravish Sankolli、M.P. Kaushik

  DOI：10.1016/j.tetlet.2012.02.087

  日期：2012.5

  A novel approach for the synthesis of N-1 substituted thiohydantoin has been developed to give quantitative yields of the desired products. The efficient synthesis of bis-thiohydantoin derivative and bicyclothiohydantoin has extended scope and applicability of present method. Solvent-free conditions and very easy work-up procedure make the reaction convenient and eco-friendly. All the products were

  已经开发出用于合成N-1取代的硫代乙内酰脲的新颖方法，以定量获得所需产物。双硫代乙内酰脲衍生物和双环硫代乙内酰脲的有效合成扩展了本方法的范围和适用性。无溶剂条件和非常简单的后处理程序使反应变得方便且环保。通过光谱技术和元素分析对所有产物进行了表征，最后通过X射线晶体学确定了代表性化合物的结构。
• Novel and green protocol for the synthesis of 2-iminohydantoins
  作者：Vinod Kumar、Hemlata Rana、M.P. Kaushik

  DOI：10.1016/j.tetlet.2012.09.057

  日期：2012.11

  A novel and green protocol for the synthesis of N-1 and C-5 substituted 2-iminohydantoins has been developed. Methyl N-cyano-N-alkyl/aryl-aminoacetate reacts with aqueous ammonia at room temperature in 10-30 min. The developed protocol does not require any work-up for the isolation or purification of the products; simple filtration can lead to the pure products in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
• US8575114B2
  申请人：——

  公开号：US8575114B2

  公开（公告）日：2013-11-05