p-amino-O,O'-bis(tert-butyldimethylsilyl)-N,N'-dihydroxybenzamidine | 1610930-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-amino-O,O'-bis(tert-butyldimethylsilyl)-N,N'-dihydroxybenzamidine
• 英文别名: 4-amino-N,N'-bis[[tert-butyl(dimethyl)silyl]oxy]benzenecarboximidamide
• CAS: 1610930-41-0
• 化学式: C₁₉H₃₇N₃O₂Si₂
• 分子量: 395.693
• InChiKey: KARQYBSTWTWUQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  68.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-amino-O,O'-bis(tert-butyldimethylsilyl)-N,N'-dihydroxybenzamidine 在 氟化铵 、 5%-palladium/activated carbon 、 钯 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、202.66 kPa 条件下， 反应 10.25h， 生成 4-氨基苯甲脒
  参考文献：
  名称：

  Synthesis of p-amino-N,N′-dihydroxybenzamidine using a TBDMS protecting group protocol

  摘要：

  A synthetic route to p-amino-N,N'-dihydroxybenzamidine is established using a TBDMS protecting group strategy starting with p-nitrobenzhydroxamic acid chloride, which is transformed to O,O'-bis(tert-butyl-dimethylsilyl)-N,N'-dihydroxybenzamidine. Reduction with sodium dithionite occurs without degradation of the dihydroxyamidine functional group. Deprotection with ammonium fluoride is fast and efficient. This is important because no other possibility to synthesize this derivative has been found up to now. Furthermore, TBDMS protecting group strategy is proved to be adaptable to other substituted N,N'-dihydroxybenzamidines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.048
• 作为产物：
  描述：

  p-nitro-O,O'-bis(tert-butyldimethylsilyl)-N,N'-dihydroxybenzamidine 在 sodium dithionite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以23%的产率得到p-amino-O,O'-bis(tert-butyldimethylsilyl)-N,N'-dihydroxybenzamidine
  参考文献：
  名称：

  Synthesis of p-amino-N,N′-dihydroxybenzamidine using a TBDMS protecting group protocol

  摘要：

  A synthetic route to p-amino-N,N'-dihydroxybenzamidine is established using a TBDMS protecting group strategy starting with p-nitrobenzhydroxamic acid chloride, which is transformed to O,O'-bis(tert-butyl-dimethylsilyl)-N,N'-dihydroxybenzamidine. Reduction with sodium dithionite occurs without degradation of the dihydroxyamidine functional group. Deprotection with ammonium fluoride is fast and efficient. This is important because no other possibility to synthesize this derivative has been found up to now. Furthermore, TBDMS protecting group strategy is proved to be adaptable to other substituted N,N'-dihydroxybenzamidines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.048

文献信息

• Synthesis of p-amino-N,N′-dihydroxybenzamidine using a TBDMS protecting group protocol
  作者：Laura Schwarz、Ulrich Girreser、Bernd Clement

  DOI：10.1016/j.tetlet.2014.04.048

  日期：2014.5

  A synthetic route to p-amino-N,N'-dihydroxybenzamidine is established using a TBDMS protecting group strategy starting with p-nitrobenzhydroxamic acid chloride, which is transformed to O,O'-bis(tert-butyl-dimethylsilyl)-N,N'-dihydroxybenzamidine. Reduction with sodium dithionite occurs without degradation of the dihydroxyamidine functional group. Deprotection with ammonium fluoride is fast and efficient. This is important because no other possibility to synthesize this derivative has been found up to now. Furthermore, TBDMS protecting group strategy is proved to be adaptable to other substituted N,N'-dihydroxybenzamidines. (C) 2014 Elsevier Ltd. All rights reserved.