diethyl (R)-1-(1-acetyl-2-oxocyclopentyl)hydrazine-1,2-dicarboxylate | 1225206-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (R)-1-(1-acetyl-2-oxocyclopentyl)hydrazine-1,2-dicarboxylate
• 英文别名: ethyl N-[(1R)-1-acetyl-2-oxocyclopentyl]-N-(ethoxycarbonylamino)carbamate
• CAS: 1225206-79-0
• 化学式: C₁₃H₂₀N₂O₆
• 分子量: 300.312
• InChiKey: SXUOQCCSCVZJAG-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-乙酰基环戊酮 、 偶氮二甲酸二乙酯 在 3-[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（1R，2R）-2-（1-哌啶基）环己基]氨基]-3-环丁烯-1,2-二酮 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以98%的产率得到diethyl (R)-1-(1-acetyl-2-oxocyclopentyl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Enantioselective α-Amination of 1,3-Dicarbonyl Compounds Using Squaramide Derivatives as Hydrogen Bonding Catalysts

  摘要：

  Catalytic enantioselective alpha-hydrazination of 1,3-dicarbonyl compounds with azodicarboxylates was investigated in the presence of our newly developed hydrogen bonding catalyst, squaramide 3j. High yields and high enantioselectivities were achieved with low catalyst loading under mild conditions.

  DOI：

  10.1021/ol1005104

文献信息

• Enantioselective α-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts
  作者：Pinar Kasaplar、Erhan Ozkal、Carles Rodríguez-Escrich、Miquel A. Pericàs

  DOI：10.1039/c5gc00496a

  日期：——

  A polymer-supported bifunctional thiourea organocatalyst (PS-TU) has been prepared and successfully used in the enantioselective alpha-amination of 1,3-dicarbonyl compounds with azodicarboxylates. In contrast with homogeneous thioureas, PS-TU is not irreversibly...

  制备了聚合物负载的双官能硫脲有机催化剂（PS-TU），并将其成功用于1,3-二羰基化合物与偶氮二羧酸酯的对映选择性α-氨基化反应。与均质的硫脲相比，PS-TU并非不可逆转...
• Copper–bipyridine-catalyzed enantioselective α-amination of β-keto esters
  作者：Subrata Ghosh、Mecheril Valsan Nandakumar、Harald Krautscheid、Christoph Schneider

  DOI：10.1016/j.tetlet.2010.02.007

  日期：2010.4

  The Cu(OTf)2-bipyridine-catalyzed, enantioselective, direct α-amination of β-keto esters and β-diketones with diethyl azodicarboxylate (DEAD) has been studied. Exceptionally high enantioselectivities of up to 99% ee were found for 1-indanone-based β-keto esters in particular even for substrates and reagents carrying conventional ester groups such as methyl and ethyl.

  研究了Cu（OTf）2-联吡啶对偶氮二甲酸二乙酯（DEAD）对β-酮酯和β-二酮的对映选择性，直接α-胺化反应。对于基于1-茚满酮的β-酮酯，特别是对于带有常规酯基（例如甲基和乙基）的底物和试剂，发现高达99％ee的极高对映选择性。
• C2-symmetric BINOL-squaramide as efficient organocatalyst for the enantioselective α-amination of 1,3-dicarbonyl compounds with dialkyl azodicarboxylates
  作者：Shi Tang、Zhi-yong Wang、Bin Liu、Chun-E. Dong

  DOI：10.1016/j.cclet.2015.03.033

  日期：2015.6

  The asymmetric a-amination of 1,3-dicarbonyl compounds with dialkyl azodicarboxylates has been achieved by C-2-symmetric BINOL-squaramide bearing multiple hydrogen bond donors to provide the desired products in excellent yields and enantioselectivities (up to 99% yield and 98% ee). (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.