diethyl (R)-1-(2-(4-bromophenyl)-1-methoxy-1-oxopropan-2-yl)hydrazine-1,2-dicarboxylate | 1245633-02-6

• 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: diethyl (R)-1-(2-(4-bromophenyl)-1-methoxy-1-oxopropan-2-yl)hydrazine-1,2-dicarboxylate
• 英文别名: methyl (2R)-2-(4-bromophenyl)-2-[ethoxycarbonyl-(ethoxycarbonylamino)amino]propanoate
• CAS: 1245633-02-6
• 化学式: C₁₆H₂₁BrN₂O₆
• 分子量: 417.257
• InChiKey: BRACQZUGEPWKBI-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (R)-1-(2-(4-bromophenyl)-1-methoxy-1-oxopropan-2-yl)hydrazine-1,2-dicarboxylate 、 五氟苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以69%的产率得到diethyl (R)-1-(1-methoxy-1-oxo-2-(2',3',4',5',6'-pentafluorobiphenyl-4-yl)propan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Asymmetric synthesis of deuterated and fluorinated aromatic α,α-disubstituted amino acid derivatives

  摘要：

  We herein present organocatalytic approaches to synthesize fluorinated and deuterated alpha-substituted phenylglycine derivatives. Whereas the addition of diethyl azodicarboxylate to fluorinated alpha-substituted aldehydes furnishes chiral non-racemic compounds, the use of chloramine-T as a nitrogen source represents a rapid access to sulfamidated fluorinated amino acid precursors. Additionally, further functionalization was achieved through the palladium-catalyzed coupling of a p-bromosubstituted aldehyde with a range of fluorine or deuterium-containing boronic acids. Oxidation of the aldehyde function and cleavage of the protection group of the nitrogen give way to the free fluorinated unnatural amino acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.026
• 作为产物：
  描述：

  、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 0.08h， 以4.68 g的产率得到diethyl (R)-1-(2-(4-bromophenyl)-1-methoxy-1-oxopropan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Asymmetric synthesis of deuterated and fluorinated aromatic α,α-disubstituted amino acid derivatives

  摘要：

  We herein present organocatalytic approaches to synthesize fluorinated and deuterated alpha-substituted phenylglycine derivatives. Whereas the addition of diethyl azodicarboxylate to fluorinated alpha-substituted aldehydes furnishes chiral non-racemic compounds, the use of chloramine-T as a nitrogen source represents a rapid access to sulfamidated fluorinated amino acid precursors. Additionally, further functionalization was achieved through the palladium-catalyzed coupling of a p-bromosubstituted aldehyde with a range of fluorine or deuterium-containing boronic acids. Oxidation of the aldehyde function and cleavage of the protection group of the nitrogen give way to the free fluorinated unnatural amino acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.026

文献信息

• Asymmetric synthesis of deuterated and fluorinated aromatic α,α-disubstituted amino acid derivatives
  作者：Caroline E. Hartmann、Thomas Baumann、Michael Bächle、Stefan Bräse

  DOI：10.1016/j.tetasy.2010.04.026

  日期：2010.6

  We herein present organocatalytic approaches to synthesize fluorinated and deuterated alpha-substituted phenylglycine derivatives. Whereas the addition of diethyl azodicarboxylate to fluorinated alpha-substituted aldehydes furnishes chiral non-racemic compounds, the use of chloramine-T as a nitrogen source represents a rapid access to sulfamidated fluorinated amino acid precursors. Additionally, further functionalization was achieved through the palladium-catalyzed coupling of a p-bromosubstituted aldehyde with a range of fluorine or deuterium-containing boronic acids. Oxidation of the aldehyde function and cleavage of the protection group of the nitrogen give way to the free fluorinated unnatural amino acids. (C) 2010 Elsevier Ltd. All rights reserved.