diethyl 1-(1-oxo-2-(4-bromophenyl)propan-2-yl)hydrazine-1,2-dicarboxylate | 1245633-09-3

• 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: diethyl 1-(1-oxo-2-(4-bromophenyl)propan-2-yl)hydrazine-1,2-dicarboxylate
• 英文别名: ethyl N-[(2R)-2-(4-bromophenyl)-1-oxopropan-2-yl]-N-(ethoxycarbonylamino)carbamate
• CAS: 1245633-09-3
• 化学式: C₁₅H₁₉BrN₂O₅
• 分子量: 387.23
• InChiKey: YPEUWOODWUAQET-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 1-(1-oxo-2-(4-bromophenyl)propan-2-yl)hydrazine-1,2-dicarboxylate 在 sodium chlorite 、 potassium dihydrogenphosphate 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 生成
  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：

  2-(4-bromophenyl)propanal 、 偶氮二甲酸二乙酯 在 三氟乙酸 、 (1R,2R)-1-(1',8'-naphthalimido)-2-aminocyclohexane 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以99%的产率得到diethyl 1-(1-oxo-2-(4-bromophenyl)propan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  第四立体中心的构建：单酰亚胺取代的环己烷-1，2-二胺催化的支链醛的不对称α-胺化

  摘要：

  据报道，由手性酰亚胺单取代的1,2-二胺衍生物催化的支链醛类的高效对映选择性α-胺化可提供优良的产率（高达99％）和对映选择性（高达ee的97％）的四级立体异构中心。手性25：668–672，2013年。©2013 Wiley Periodicals，Inc

  DOI：

  10.1002/chir.22203

文献信息

• Construction of Quaternary Stereocenters: Asymmetric α-Amination of Branched Aldehydes Catalyzed by Monoimide Substituted Cyclohexane-1,2-Diamines
  作者：Ji-Ya Fu、Qi-Lin Wang、Lin Peng、Yong-Yuan Gui、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1002/chir.22203

  日期：2013.10

  A highly efficient enantioselective α‐amination of branched aldehydes catalyzed by chiral imide monosubstituted 1,2‐diamine derivatives was reported to afford the quaternary stereogenic centers in excellent yields (up to 99%) and enantioselectivities (up to 97% ee). Chirality 25:668–672, 2013. © 2013 Wiley Periodicals, Inc

  据报道，由手性酰亚胺单取代的1,2-二胺衍生物催化的支链醛类的高效对映选择性α-胺化可提供优良的产率（高达99％）和对映选择性（高达ee的97％）的四级立体异构中心。手性25：668–672，2013年。©2013 Wiley Periodicals，Inc
• 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.