(3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one | 115828-87-0

• 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: (3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (3R,4R)-4-((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 115828-87-0
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: ZRMYROHIJHDIBO-FRRDWIJNSA-N

物化性质

• 沸点：
  534.1±50.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one 在 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 (3R,4S)-4-[(1S)-1,2-dihydroxyethyl]-3-(methoxymethoxy)-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  PYRIDINE DERIVATIVES

  摘要：

  公开号：

  EP3228616B1
• 作为产物：
  描述：

  N-(4-methoxyphenyl)-2,3-O-isopropylidene-D-glyceraldehyde imine 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.33h， 生成 (3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Metal-Mediated Carbonyl-1,3-butadien-2-ylation by 1,4-Bis(methanesulfonyl)-2-butyne or 1,4-Dibromo-2-butyne in Aqueous Media:  Asymmetric Synthesis of 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methanesulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.

  DOI：

  10.1021/jo016247b

文献信息

• Preparation of chiral 3-unsubstituted β-lactams from 3-hydroxy β-lactams by using the alkoxyketene-imine cycloaddition reaction as an approach to the azetidinone ring: A formal synthesis of the carbapenem antibiotic (+)-PS-5.
  作者：Claudio Palomo、Fernando P. Cossío、Jesús M. Ontoria、José M. Odriozola

  DOI：10.1016/0040-4039(91)80701-7

  日期：1991.6

  Formation of chiral 3-hydroxy β-lactams from the alkoxyketene-imine cycloaddition reaction followed by deoxygenation under Barton's conditions provided a simple roam to optically active 3-unsubstituted β-lactams.

  由烷氧基乙烯酮-亚胺环加成反应形成手性3-羟基β-内酰胺，然后在巴顿条件下进行脱氧，为光学活性的3-未取代的β-内酰胺提供了简单的漫游条件。
• Microwave-induced organic reaction enhancement chemistry.4 convenient synthesis of enantiopure α-hydroxy-β-lactams1
  作者：Bimal K. Banik、Maghar S. Manhas、Zbignew Kaluza、Khaled J. Barakat、Ajay K. Rose

  DOI：10.1016/s0040-4039(00)92513-9

  日期：1992.6

  A convenient and rapid synthesis of enantiopure α-hydroxy-β-lactams using microwave-induced organic reaction enhancement chemistry has been developed. Reactions in domestic microwave ovens, which are very convenient and economical for small scale work in research or teaching laboratories, can also be conducted on a preparative scale of 100–500g in simple beakers or flasks.

  已经开发了利用微波诱导的有机反应增强化学方便快速地合成对映体纯的α-羟基-β-内酰胺的方法。对于研究或教学实验室中的小规模工作而言，家用微波炉的反应非常方便且经济，也可以在简单的烧杯或烧瓶中以100–500 g的制备规模进行反应。
• An Efficient Synthesis of 2,3-Aziridino-γ-lactones from Azetidin-2-ones
  作者：Abdul Rakeeb Deshmukh、Ajaykumar S. Kale

  DOI：10.1055/s-2005-872263

  日期：——

  An efficient synthesis ofenantiopure 2,3-aziridino-γ-lactones from azetidin-2-ones is described. Acid-catalyzed tandem intramolecular azetidinone ring opening followed by aziridine ring formation via elimination of a mesylate group is the key step in this synthesis. 2,3-Aziridino-y-lactones are important precursors for biologically important glulamic acid derivatives.

  描述了一种从 azetidin-2-ones 有效合成对映体纯 2,3-aziridino-γ-内酯的方法。酸催化串联分子内氮杂环丁酮开环，然后通过消除甲磺酸酯基团形成氮丙啶环是该合成中的关键步骤。2,3-Aziridino-y-内酯是生物学上重要的谷氨酸衍生物的重要前体。
• Stereospecific novel glycosylation of hydroxy ?-lactams via iodine-catalyzed reaction: a new method for optical resolution
  作者：Bimal K. Banik、Maghar S. Manhas

  DOI：10.1016/j.tet.2012.01.078

  日期：2012.12

  Glycosylation of racemic and optically active α-hydroxy β-lactams by reaction with a few glycal derivatives in the presence of catalytic amounts of iodine has provided stereospecific formation of α-glycosides. This method has been extended for the preparation of optically active hydroxy β-lactams in excellent yields. The stereochemistry and nature of the glycals as well as the stereochemistry of the

  在催化量的碘存在下，通过与一些糖基衍生物反应，使外消旋和旋光性α-羟基β-内酰胺糖基化，形成了α-糖苷的立体定向形成。该方法已经扩展到以优异的产率制备光学活性的羟基β-内酰胺。糖基的立体化学和性质以及β-内酰胺环的立体化学对有效糖基化具有深远的影响。
• Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines-An Experimental and Computational Approach
  作者：Nicola Piens、Hannelore Goossens、Dietmar Hertsen、Sari Deketelaere、Lieselotte Crul、Lotte Demeurisse、Jelle De Moor、Elias Van den Broeck、Karen Mollet、Kristof Van Hecke、Veronique Van Speybroeck、Matthias D'hooghe

  DOI：10.1002/chem.201703852

  日期：2017.12.19

  The reactivity of 3‐oxo‐β‐lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin‐2‐one C4 substituent, this reaction was shown to selectively produce 3‐imino‐β‐lactams (through dehydration), α‐aminoamides (through CO elimination), or ethanediamides (through an unprecedented C3−C4 ring opening). In addition to the experimental results, the mechanisms and

  深入研究了3-氧代-β-内酰胺相对于伯胺的反应性。取决于特定的氮杂环丁烷-2-酮C4取代基，该反应可选择性产生3-亚氨基-β-内酰胺（通过脱水），α-氨基酰胺（通过CO消除）或乙二酰胺（通过前所未有的C3-C4环）开幕）。除了实验结果外，还通过DFT计算方法研究并阐明了控制这些特殊转化的机制和因素。