trans-1-benzyl-3-amino-4-methyl-β-azetidinone | 106502-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: trans-1-benzyl-3-amino-4-methyl-β-azetidinone
• 英文别名: trans-1-benzyl-3-amino-4-methyl-2-azetidinone；(3R,4R)-3-amino-1-benzyl-4-methylazetidin-2-one
• CAS: 106502-02-7；106520-18-7；124816-66-6；124816-68-8；124816-74-6；124816-75-7；135027-33-7；135027-34-8
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: IDKVWYIXOZZERZ-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-1-benzyl-3-amino-4-methyl-β-azetidinone 、 乙酸酐 生成 N-((2R,3R)-1-Benzyl-2-methyl-4-oxo-azetidin-3-yl)-acetamide
  参考文献：
  名称：

  TUFARIELLO, JOSEPH J.;PINTO, DONALD J. P.;MILOWSKY, ARNOLD S.;REINHARDT, +, TETRAHEDRON LETT., 28,(1987) N 45, 5481-5484

  摘要：

  DOI：
• 作为产物：
  描述：

  N-ethylidenebenzylamine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 trans-1-benzyl-3-amino-4-methyl-β-azetidinone
  参考文献：
  名称：

  从N保护的α-氨基酸酯和亚胺的烯醇锌中反式-3-氨基-β-内酰胺的立体选择性一锅合成。

  摘要：

  报道了一种新的一锅法合成3-氨基β-内酰胺的方法，该方法基于简单的亚胺与二甲硅烷基保护的甘氨酸酯的烯醇锌的缩合反应。分离的产率高并且观察到反式选择性。

  DOI：

  10.1016/s0040-4039(00)87909-5

文献信息

• Synthesis of optically active .beta.-lactams by the photolytic reaction of imines with optically active chromium carbene complexes
  作者：Louis S. Hegedus、Rene Imwinkelried、Marie Alarid-Sargent、Dalimil Dvorak、Yoshitaka Satoh

  DOI：10.1021/ja00159a034

  日期：1990.1

  Optically active chromium carbene complexes utilizing (S)-valine- and (R)-phenylglycine-derived chiral auxillaries were synthesized and subjected to photolytic reaction with a number of imines. Optically active β-lactams were produced in good to excellent chemical yield and with high diastereoisomeric excess. Procedures for removal of the chiral auxilliary to produce the optically active free amino

  利用 (S)-缬氨酸和 (R)-苯基甘氨酸衍生的手性助剂合成了光学活性铬卡宾配合物，并与多种亚胺进行光解反应。光学活性 β-内酰胺以良好到极好的化学产率和高非对映异构体过量生产。开发了去除手性助剂以生产光学活性游离氨基 β-内酰胺的程序
• A new and efficient route to 3-amino-2-azetidinones via zinc enolates of N,N-disubstituted glycine esters
  作者：Fred H. Van der Steen、Henk Kleijn、Johann T. B. H. Jastrzebski、Gerard Van Koten

  DOI：10.1021/jo00017a030

  日期：1991.8

  This report describes novel and efficient ''one-pot'' syntheses of 1-unsubstituted-3-amino-4-substituted-2-azetidinones (8 and 9) involving the in situ preparation of lithium and particularly zinc enolates (5 and 6, respectively) of N,N-disubstituted glycine esters (4) and subsequent reactions of these enolates with (simple) imines (7). Lithium enolates 5 only react with activated imines that are N-substituted with an electron-withdrawing group (e.g. aryl, trialkylsilyl), affording cis-3-amino-2-azetidinones in excellent yields with moderate to good stereoselectivity (de 68-92%). Zinc enolates 6 are more generally applicable since they react with activated imines as well as unactivated imines (e.g. those which are N-substituted with an electron-donating group such as alkyl) to afford 3-amino-2-azetidinones in excellent yields. The trans diastereoselectivity of the zinc-mediated enolate-imine condensation can be tuned by changing the steric and electronic properties of the substituents of the reagents (i.e. both enolate and imine), as well as the solvent polarity. The observed stereoselectivities are explained in terms of two highly ordered transition states, consisting of a Z-zinc ester enolate and an E-imine. Protection of the amino function of the metal enolates as a 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane ring affords 2-azetidinone products that can be easily deprotected to provide a free 3-amino function. In this way, trans-1-benzyl-3-(protected amino)-4-methyl-2-azetidinone (9a) and trans-3-(protected amino)-4-[(trimethylsilyl)ethynyl]-2-azetidinone (9g), key intermediates in the synthesis of Aztreonam (and 9g for bicyclic beta-lactam antibiotics as well), have been prepared in excellent yields (98 and 93%, respectively) with a high diastereoselectivity (de 82 and 94%, respectively). Furthermore, depending on the reactivity of imines 7, our method is also applicable using a catalytic amount (10 mol %) of ZnCl2.
• Synthesis of amino-.beta.-lactams by the photolytic reaction of imines with pentacarbonyl[(dibenzylamino)carbene]chromium(0)
  作者：Christian Borel、Louis S. Hegedus、Jurg Krebs、Yoshitaka Satoh

  DOI：10.1021/ja00238a018

  日期：1987.2