(R)-di-tert-butyl 1-(2-(4-bromophenyl)-1-oxo-propan-2-yl)hydrazine-1,2-dicarboxylate | 1304668-78-7

• 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: (R)-di-tert-butyl 1-(2-(4-bromophenyl)-1-oxo-propan-2-yl)hydrazine-1,2-dicarboxylate
• 英文别名: tert-butyl N-[(2R)-2-(4-bromophenyl)-1-oxopropan-2-yl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbamate
• CAS: 1304668-78-7
• 化学式: C₁₉H₂₇BrN₂O₅
• 分子量: 443.338
• InChiKey: ZGHVLHMAXSVHIC-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-溴苯基)-2-甲基-环氧乙烷 在 三氟化硼乙醚 、 (S)-4-(叔丁氧基)-2-甲基-4-氧代丁酸 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 (R)-di-tert-butyl 1-(2-(4-bromophenyl)-1-oxo-propan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  β-tert-Butyl aspartate as an organocatalyst for the asymmetric α-amination of α,α-disubstituted aldehydes

  摘要：

  The enantioselective alpha-amination reaction of alpha,alpha-disubstituted aldehydes can lead to a variety of enantioenriched amino aldehydes, amino alcohols, and amino acids. After screening a variety of amino acids and their derivatives, we identified a cheap, simple, commercially available aspartic acid derivative that can catalyze efficiently the reaction between alpha,alpha-disubstituted aldehydes and dialkyl azodicarboxylates. The reaction proceeds smoothly leading to the corresponding alpha-aminated adducts in moderate to quantitative yields and moderate to high enantioselectivities (up to 96% ee). Finally, the conversion of these adducts to alpha,alpha-disubstituted quaternary amino acids is also described. 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.103

文献信息

• β-tert-Butyl aspartate as an organocatalyst for the asymmetric α-amination of α,α-disubstituted aldehydes
  作者：Alexis Theodorou、Giorgos N. Papadopoulos、Christoforos G. Kokotos

  DOI：10.1016/j.tet.2013.04.103

  日期：2013.7

  The enantioselective alpha-amination reaction of alpha,alpha-disubstituted aldehydes can lead to a variety of enantioenriched amino aldehydes, amino alcohols, and amino acids. After screening a variety of amino acids and their derivatives, we identified a cheap, simple, commercially available aspartic acid derivative that can catalyze efficiently the reaction between alpha,alpha-disubstituted aldehydes and dialkyl azodicarboxylates. The reaction proceeds smoothly leading to the corresponding alpha-aminated adducts in moderate to quantitative yields and moderate to high enantioselectivities (up to 96% ee). Finally, the conversion of these adducts to alpha,alpha-disubstituted quaternary amino acids is also described. 2013 Elsevier Ltd. All rights reserved.