1-(pyridin-4-yl)-2,3-di(tert-butoxycarbonyl)guanidine | 1286277-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(pyridin-4-yl)-2,3-di(tert-butoxycarbonyl)guanidine
• 英文别名: tert-butyl N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-pyridin-4-ylcarbamimidoyl]carbamate
• CAS: 1286277-82-4
• 化学式: C₁₆H₂₄N₄O₄
• 分子量: 336.391
• InChiKey: OQWCIPMJGASVGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(pyridin-4-yl)-2,3-di(tert-butoxycarbonyl)guanidine 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(吡啶-4-基)胍
  参考文献：
  名称：

  Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 1: 2-Pyridinylguanidines

  摘要：

  The identification of 2-pyridinylguanidines (e.g. 27 and 28) as selective inhibitors of urokinase-type plasminogen activator (uPA) is described. The X-ray crystal structure of 27 has been determined, and modelling has been used to predict binding in the enzyme active site. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00701-6
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydride 、 三乙胺 、 copper dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 16.5h， 生成 1-(pyridin-4-yl)-2,3-di(tert-butoxycarbonyl)guanidine
  参考文献：
  名称：

  Copper(II) chloride promoted transformation of amines into guanidines and asymmetrical N,N′-disubstituted guanidines

  摘要：

  We present a concise, less-toxic and broadly applicable method for coupling weakly nucleophilic amines with N,N'-di-(tert-butoxycarbonyl)thiourea, N-(tert-butxoycarbonyl), N'-alkyl/arylsubstituted-thioureas and N,N'-di-(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of copper(II) chloride. Subsequent removal of Boc protecting groups affords guanidines, di-substituted guanidines and 2-aminoimidazolines in modest to excellent overall yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.070

文献信息

• Copper(II) chloride promoted transformation of amines into guanidines and asymmetrical N,N′-disubstituted guanidines
  作者：Brendan Kelly、Isabel Rozas

  DOI：10.1016/j.tetlet.2013.05.070

  日期：2013.7

  We present a concise, less-toxic and broadly applicable method for coupling weakly nucleophilic amines with N,N'-di-(tert-butoxycarbonyl)thiourea, N-(tert-butxoycarbonyl), N'-alkyl/arylsubstituted-thioureas and N,N'-di-(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of copper(II) chloride. Subsequent removal of Boc protecting groups affords guanidines, di-substituted guanidines and 2-aminoimidazolines in modest to excellent overall yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Selective urokinase-type plasminogen activator (uPA) inhibitors. Part 1: 2-Pyridinylguanidines
  作者：Christopher G Barber、Roger P Dickinson、Valerie A Horne

  DOI：10.1016/s0960-894x(01)00701-6

  日期：2002.1

  The identification of 2-pyridinylguanidines (e.g. 27 and 28) as selective inhibitors of urokinase-type plasminogen activator (uPA) is described. The X-ray crystal structure of 27 has been determined, and modelling has been used to predict binding in the enzyme active site. (C) 2002 Elsevier Science Ltd. All rights reserved.