(R)-di-isopropyl 1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate | 1256965-85-1

• 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-isopropyl 1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate
• 英文别名: Diisopropyl (R)-1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate；(R)-2-[N,N'-bis(isopropyloxycarbonyl)hydrazino]-2-phenylpropionaldehyde；propan-2-yl N-[(2R)-1-oxo-2-phenylpropan-2-yl]-N-(propan-2-yloxycarbonylamino)carbamate
• CAS: 1256965-85-1
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: AHXCARKKVOLOSH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (R)-di-isopropyl 1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以92 %的产率得到(R)-3-isopropoxycarbonylamino-4-methyl-4-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  无溶剂条件下α,α-二取代醛的有机催化对映选择性α-氮化

  摘要：

  开发了一种由手性氨基甲酸酯单保护环己-1,2-二胺作为有机催化剂促进的 α,α-二取代醛与偶氮二羧酸盐的高效对映选择性 α-氮化方法。该过程在没有任何溶剂的情况下进行，并以优异的收率和高达 99% ee的对映选择性获得了相应的 α,α-二取代的 α- 硝化醛。该程序的可持续性是通过计算绿色指标（例如 EcoScale 和 E-factor）来确定的。此外，理论计算已被用来证明获得的对映选择性意义。

  DOI：

  10.1021/acs.joc.2c01919
• 作为产物：
  描述：

  2-苯基丙醛 、 偶氮二甲酸二异丙酯 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 4.0h， 以94%的产率得到(R)-di-isopropyl 1-(1-oxo-2-phenylpropan-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
• 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.
• Primary amine catalyzed electrophilic amination of α,α-disubstituted aldehydes
  作者：Alaric Desmarchelier、Hasret Yalgin、Vincent Coeffard、Xavier Moreau、Christine Greck

  DOI：10.1016/j.tetlet.2011.06.063

  日期：2011.8

  Organocatalytic alpha-amination of alpha,alpha-disubstituted aldehydes promoted by 9-amino-(9-deoxy)-epi-quinine is described. alpha-Hydrazino aldehydes bearing a quaternary stereogenic center are obtained in good to excellent yields and enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.
• A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes
  作者：Michael R. Witten、Eric N. Jacobsen

  DOI：10.1021/acs.orglett.5b01193

  日期：2015.6.5

  A new primary amine catalyst for the asymmetric a-hydroxylation and a-fluorination of alpha-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for a-functionalizations. Promising initial results in alpha-amination and alpha-chlorination reactions support this hypothesis.
• Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent
  作者：Alejandro Torregrosa-Chinillach、Asier Carral-Menoyo、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.1021/acs.joc.2c01919

  日期：2022.11.4

  of α,α-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2-diamine as organocatalyst has been developed. The process was carried out without any solvent, and the corresponding α,α-disubstituted α-nitrogenated aldehydes were obtained with excellent yields and enantioselectivities up to 99% ee. The sustainability of the procedure was established through

  开发了一种由手性氨基甲酸酯单保护环己-1,2-二胺作为有机催化剂促进的 α,α-二取代醛与偶氮二羧酸盐的高效对映选择性 α-氮化方法。该过程在没有任何溶剂的情况下进行，并以优异的收率和高达 99% ee的对映选择性获得了相应的 α,α-二取代的 α- 硝化醛。该程序的可持续性是通过计算绿色指标（例如 EcoScale 和 E-factor）来确定的。此外，理论计算已被用来证明获得的对映选择性意义。