(-)-N,N'-bis(ethoxycarbonyl)-2-hydrazino-2-(2'-naphthyl)-propionaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-N,N'-bis(ethoxycarbonyl)-2-hydrazino-2-(2'-naphthyl)-propionaldehyde
• 英文别名: ethyl N-(ethoxycarbonylamino)-N-[(2R)-2-naphthalen-2-yl-1-oxopropan-2-yl]carbamate
• 化学式: C₁₉H₂₂N₂O₅
• 分子量: 358.394
• InChiKey: JLYQPAMLBRZBAA-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  甲氧基甲基三苯基氯化膦 在 L-脯氨酸 sodium hydride 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 60.0h， 生成 (-)-N,N'-bis(ethoxycarbonyl)-2-hydrazino-2-(2'-naphthyl)-propionaldehyde
  参考文献：
  名称：

  Proline-catalysed asymmetric amination of α,α-disubstituted aldehydes: synthesis of configurationally stable enantioenriched α-aminoaldehydes

  摘要：

  脯氨酰催化的α,α-二取代外消旋醛与叠氮羧酸酯的氨化反应顺利进行，产生构型稳定的非外消旋醛和噁唑啉酮，最高可达86%的ee值。

  DOI：

  10.1039/b305465a

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
• Enantioselective α-Amination of Branched Aldehydes Promoted by Simple Chiral Primary Amino Acids
  作者：Ji-Ya Fu、Qing-Chuan Yang、Qi-Lin Wang、Jun-Nan Ming、Fei-Ying Wang、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1021/jo102361h

  日期：2011.6.3

  A series of simple chiral primary amino acids were first successfully applied to promote the enantioselective α-amination of branched aldehydes with azadicarboxylates and the desired adducts bearing quaternary stereogenic centers were obtained in excellent yields (up to 99%) and enantioselectivities (up to 97% ee).

  首先成功地应用了一系列简单的手性伯氨基酸，以促进氮杂二羧酸与支链醛的对映选择性α-氨基化反应，并以优异的收率（高达99％）和对映选择性（高达97％）获得了带有季立体中心的所需加合物。 ee）。
• Effective construction of quaternary stereocenters by highly enantioselective α-amination of branched aldehydes
  作者：Ji-Ya Fu、Xiao-Ying Xu、Yan-Chun Li、Qing-Chun Huang、Li-Xin Wang

  DOI：10.1039/c0ob00406e

  日期：——

  A highly efficient enantioselective α-amination of branched aldehydes with azadicarboxylates promoted by chiral proline-derived amide thiourea bifunctional catalysts was developed for the first time, affording the adducts bearing quaternary stereogenic centers with excellent yields (up to 99%) and enantioselectivities (up to 97% ee).

  首次开发了由手性脯氨酸衍生的酰胺硫脲双功能催化剂促进的氮杂二羧酸与支链醛的高效对映选择性α-胺化反应，使带有季立体中心的加合物具有优异的收率（高达99％）和对映选择性（高达97％ee）。
• Chiral α-Arylethanamines: An Organocatalyst for the Enantioselective α-Amination of Branched Aldehydes
  作者：Ji-Ya Fu、Qi-Lin Wang、Lin Peng、Yong-Yuan Gui、Fan Wang、Fang Tian、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1002/ejoc.201201701

  日期：2013.5

  α-Arylethanamines were investigated as organocatalysts for the α-amination of branched aldehydes with azodicarboxylates. Optimization identified (R)-1-(1-naphthyl)ethanamine (1g) as an effective and enantioselective organocatalyst; multifunctional chiral quaternary amino aldehydes were successfully obtained in excellent yields (up to 99 %) and with excellent enantioselectivities (up to 98 % ee).

  α-芳基乙醇胺被研究作为有机催化剂用于支链醛与偶氮二羧酸酯的 α-胺化。优化确定 (R)-1-(1-萘基) 乙胺 (1g) 是一种有效的对映选择性有机催化剂；以优异的产率（高达 99 %）和优异的对映选择性（高达 98 % ee）成功获得了多功能手性季氨基醛。
• Thermal Effects in the Organocatalytic Asymmetric α-Amination of Disubstituted Aldehydes with Azodicarboxylates: A High-Temperature Organocatalysis
  作者：Thomas Baumann、Michael Bächle、Caroline Hartmann、Stefan Bräse

  DOI：10.1002/ejoc.200701167

  日期：2008.5

  This article describes the thermally accelerated organocatalytic α-amination of disubstituted aldehydes with azodicarboxylates under microwave conditions. Compared to the results previously obtained at room temperature, both yield and enantioselectivity could be significantly increased. Employing microwave irradiation resulted in a considerably reduced reaction time. Therefore, this improved protocol

  这篇文章描述了在微波条件下双取代醛与偶氮二羧酸酯的热加速有机催化 α-胺化。与先前在室温下获得的结果相比，产率和对映选择性都可以显着提高。采用微波辐射导致反应时间显着减少。因此，这种改进的协议允许快速有效地合成 α,α-二取代氨基醛，并为迄今为止二取代醛的 α-胺化提供了最佳结果。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)