N-benzyl-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methanimine oxide | 121701-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methanimine oxide
• CAS: 121701-23-3
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: SBWVZNCDVKIVPK-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl ethynylphosphonate 、 N-benzyl-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methanimine oxide 在 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 72.25h， 以58%的产率得到diethyl (R)-trans-1-benzyl-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxoazetidine-3-phosphonate
  参考文献：
  名称：

  乙炔膦酸二乙酯在Kinugasa反应合成3-膦酰化β-内酰胺中的应用

  摘要：

  容易获得的乙炔基膦酸二乙酯在室温下在衣笠反应条件下与各种醛硝酮反应，以良好的产率提供 3-膦酰化的 β-内酰胺。在所有情况下，反应仅导致反式异构体。基于 1 H-NMR 光谱分析指定反式构型。

  DOI：

  10.3998/ark.5550190.p009.660
• 作为产物：
  描述：

  (S)-(-)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯 在 二异丁基氢化铝 作用下， 生成 N-benzyl-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methanimine oxide
  参考文献：
  名称：

  Diastereoselective synthesis of β-lactams via Kinugasa reaction of acyclic chiral nitrones

  摘要：

  An approach to beta-lactams via a Kinugasa reaction between chiral copper acetylides and chiral acyclic nitrones bearing either 1,3-dioxane or 1,3-dioxolane moieties is reported. The stereochemical preferences observed in these reactions are discussed. The reaction provides access to a variety of interesting beta-lactam structures. Electronic circular dichroism in combination with NMR spectroscopy was shown to be a useful and effective method for the reliable determination of the absolute configuration of all components of a complex mixtures of azetidinones. The effectiveness of the chiral analysis of complex mixtures was demonstrated for HPLC coupled on-line with electronic circular dichroism detection as well. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.11.006

文献信息

• Diastereoselective synthesis of propargylic N-hydroxylamines via NHC–copper(<scp>i</scp>) halide-catalyzed reaction of terminal alkynes with chiral nitrones on water
  作者：Ł. Woźniak、O. Staszewska-Krajewska、M. Michalak

  DOI：10.1039/c4cc08742a

  日期：——

  first NHC-copper(I)-halide catalyzed addition of terminal alkynes to enantiomerically pure nitrones on water is described. This reaction provides a straightforward access to propargylic N-hydroxylamines in excellent yield and with excellent stereoselectivity (up to 97%). The presented methodology was applied as a key step in the formal synthesis of (-)-lentiginosine.

  描述了NHC-铜（I）-卤化物在水上对映体纯的硝酮的第一催化的末端炔烃的加成。该反应以优异的产率和优异的立体选择性（高达97％）提供了直接进入炔丙基N-羟胺的途径。所提出的方法被用作（-）-龙胆草碱的形式合成中的关键步骤。
• Internally Protected Amino Sugar Equivalents from Enantiopure 1,2‐Oxazines: Synthesis of Variably Configured Carbohydrates with C‐Branched Amino Sugar Units
  作者：Fabian Pfrengle、Hans‐Ulrich Reissig

  DOI：10.1002/chem.201001060

  日期：2010.10.18

  precursors allowed the synthesis of homo‐oligomeric di‐ and trisaccharides 44, 46 and 47 or a hybrid trisaccharide 51 with natural carbohydrates. Access to a bivalent amino sugar derivative 54 was accomplished by reaction of rearrangement product 10 with 1,5‐pentanediol. Alternatively, when a protected L‐serine derivative was employed as glycosyl acceptor, the glycosylated amino acid 60 was efficiently prepared

  完成了立体构型合成不同构型的C2支链的4-氨基糖衍生物。路易斯酸介导的苯硫基取代的1,2-恶嗪的重排提供了可直接用于糖苷化反应的糖基供体等价物。甲醇处理内部提供保护的已转化成立体异构甲基糖苷氨基糖当量28，耳鼻喉科- 28，29，耳鼻喉科- 29和34在两个简单的还原步骤。与天然碳水化合物或双环氨基糖前体的反应可以合成同低聚二糖和三糖44，46和47或杂三糖51与天然碳水化合物。通过重排产物10与1,5-戊二醇的反应，可以得到二价氨基糖衍生物54。另外，当采用受保护的L-丝氨酸衍生物作为糖基受体时，只需几步即可有效地制备糖基化氨基酸60。在本报告中，我们描述了由对映体纯的1,2-恶嗪合成不寻常的氨基糖结构单元的方法，这些结构单元可以与天然碳水化合物或天然产物糖苷配基连接，以生产具有潜在化学药物用途的新的天然产物类似物。
• Application of diethyl ethynephosphonate for the synthesis of 3-phosphonylated β-lactams via Kinugasa reaction
  作者：Marcin K. Kowalski、Grzegorz Mlostoń、Emilia Obijalska、Heinz Heimgartner

  DOI：10.3998/ark.5550190.p009.660

  日期：——

  The easily available diethyl ethynylphosphonate reacts with diverse aldonitrones under Kinugasa reaction conditions at room temperature, providing 3-phosphonylated beta-lactams in good yields. In all cases, the reaction led to the trans-isomer exclusively. The trans-configuration was assigned based on 1H-NMR spectroscopic analysis.

  容易获得的乙炔基膦酸二乙酯在室温下在衣笠反应条件下与各种醛硝酮反应，以良好的产率提供 3-膦酰化的 β-内酰胺。在所有情况下，反应仅导致反式异构体。基于 1 H-NMR 光谱分析指定反式构型。
• Diastereoselective synthesis of β-lactams via Kinugasa reaction of acyclic chiral nitrones
  作者：Łukasz Mucha、Kamil Parda、Olga Staszewska-Krajewska、Sebastian Stecko、Artur Ulikowski、Jadwiga Frelek、Agata Suszczyńska、Marek Chmielewski、Bartłomiej Furman

  DOI：10.1016/j.tetasy.2015.11.006

  日期：2016.1

  An approach to beta-lactams via a Kinugasa reaction between chiral copper acetylides and chiral acyclic nitrones bearing either 1,3-dioxane or 1,3-dioxolane moieties is reported. The stereochemical preferences observed in these reactions are discussed. The reaction provides access to a variety of interesting beta-lactam structures. Electronic circular dichroism in combination with NMR spectroscopy was shown to be a useful and effective method for the reliable determination of the absolute configuration of all components of a complex mixtures of azetidinones. The effectiveness of the chiral analysis of complex mixtures was demonstrated for HPLC coupled on-line with electronic circular dichroism detection as well. (C) 2015 Elsevier Ltd. All rights reserved.