(3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one | 103174-02-3

• 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,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• 英文别名: (3R,4S)-3-acetoxy-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(4-methoxyphenyl)-2-azetidinone；(+)-(3R,4S)-cis-3-acetoxy-1-(p-methoxyphenyl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone；(+)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(p-methoxyphenyl)-2-azetidinone；cis-3-acetoxy-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)azetidin-2-one；[(2S,3R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl] acetate
• CAS: 103174-02-3
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: OVYOJVALBIYHSJ-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.03h， 以90%的产率得到
  参考文献：
  名称：

  Yadav, Ram Naresh; Banik, Indrani; Banik, Bimal Krishna, Journal of the Indian Chemical Society, 2018, vol. 95, # 11, p. 1401 - 1403

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以88%的产率得到(3R,4S)-cis-1-(p-anisyl)-3-acetoxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
  参考文献：
  名称：

  通过2-氮杂环丁酮系链的烯醛的分子内硝酮-烯烃环加成反应快速进入对映纯多环β-内酰胺

  摘要：

  New enantiomerically pure fused 2 or bridged 3 polycyclic beta-lactam systems are regio- and stereoselectively prepared via intramolecular nitrene-alkene cycloaddition of 2-azetidinone-tethered alkenyl-aldehydes 1. The regioselectivity of the cycloaddition can be tuned by moving the alkene substituent from N1 to C3 on the 2-azetidinone ring. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01013-8

文献信息

• 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。
• An Expeditious Route for the Synthesis of Oxazepine Triazolo-β-Lactams through Intramolecular Metal-Free [3+2] Azide–Alkyne Cycloaddition
  作者：Ram N. Yadav、Sunena Chandra、Armando Paniagua、Md. Firoj Hossain、Bimal Krishna Banik

  DOI：10.1071/ch19670

  日期：——

  A copper-free intramolecular azide–alkyne cycloaddition reaction of 4-hydroxymethyl-β-lactam with sodium azide has been described. The present approach involves the incorporation of an alkyne moiety through O-alkynylation of 3-hydroxy β-lactam with various propargylic halides. The generality of the method has been demonstrated by treating the corresponding tosylates or mesylates of the hydroxymethyl

  已经描述了 4-羟甲基-β-内酰胺与叠氮化钠的无铜分子内叠氮化物-炔烃环加成反应。本方法涉及通过3-羟基β-内酰胺与各种炔丙基卤化物的O-炔基化结合炔部分。通过在一锅三步反应中用叠氮化钠处理各种β-内酰胺连接的末端和内部炔烃的羟甲基官能团的相应甲苯磺酸盐或甲磺酸盐来证明该方法的普遍性，以提供新的oxazep​​ane-β -内酰胺融合的三唑支架具有不同的兴趣，产量高。
• Asymmetric synthesis of α-keto β-lactams via [2+2] cycloaddition reaction: A concise approach to optically active (α-hydroxy β-lactams and β-alkyl(aryl)isoserines.
  作者：Claudio Palomo、Jesús M. Aizpurua、José I. Miranda、Antonia Mielgo、José M. Odriozola

  DOI：10.1016/s0040-4039(00)73743-9

  日期：1993.9

  The cycloaddition reaction of the Evans-Sjögren ketenes to imines, followed by α-hydroxylation of the resulting cycloadducts provides an efficient general asymmetric synthesis of α-keto β-lactams and derivatives.

  Evans-Sjögren烯酮与亚胺的环加成反应，然后对所得的环加合物进行α-羟基化反应，可有效地进行α-酮基β-内酰胺及其衍生物的一般不对称合成。
• Stereoselective Allylation of 4-Oxoazetidine-2-carbaldehydes. Application to the Stereocontrolled Synthesis of Fused Tricyclic β-Lactams via Intramolecular Diels−Alder Reaction of 2-Azetidinone-Tethered Trienes
  作者：Benito Alcaide、Pedro Almendros、Nati R. Salgado

  DOI：10.1021/jo991641j

  日期：2000.6.1

  Allylation reactions of racemic and optically pure 4-oxoazetidine-2-carbaldehydes were investigated both under anhydrous conditions and in aqueous media. Different Lewis acid or metal mediators showed varied diastereoselectivities on product formation during allylation reactions of the above aldehydes with allyltrimethylsilane, allyltributylstannane, or allyl bromide. Under standard reaction conditions

  在无水条件下和在水性介质中均研究了外消旋和光学纯的4-氧杂氮杂环丁烷-2-甲醛的烯丙基化反应。在上述醛与烯丙基三甲基硅烷，烯丙基三丁基锡烷或烯丙基溴的烯丙基化反应期间，不同的路易斯酸或金属介体在产物形成过程中表现出不同的非对映选择性。在标准反应条件下，氯化锡（IV）促进将烯丙基三甲基硅烷添加到4-氧杂氮杂环丁烷-2-甲醛中，提供了最高的非对映选择性和最佳收率。烯丙基三丁基锡烷的三氟化硼-乙醚促进的反应提供了较低的非对映选择性，同时具有相同的面部偏好。铟促进的烯丙基化显示出相反的非对面优先性，尽管观察到的选择性在合成上不是有用的。这些均烯丙基醇的甲磺酸酯用于顺式-4-丁二烯基-2-氮杂环丁酮的立体选择性制备。有趣的是，在密封管中与等分子量的DBU在甲苯中加热时，在β-内酰胺环的1或3位上具有额外烯烃或炔烃系链的甲磺酸酯，可通过串联一锅消除反应制得稠合的三环2-氮杂环丁酮。分子内Diels-Alder反应。
• N1–C4 β-Lactam Bond Cleavage in the 2-(Trimethylsilyl)thiazole Addition to β-Lactam Aldehydes: Asymmetric Synthesis of Spiranic and Tertiary α-Alkoxy-γ-keto Acid Derivatives
  作者：Benito Alcaide、Pedro Almendros、María C. Redondo

  DOI：10.1002/ejoc.200700231

  日期：2007.8

  Starting substrates, enantiopure spiranic or 3-substituted 3-alkoxy-4-oxoazetidine-2-carbaldehydes, were prepared from (R)-2,3-O-isopropylideneglyceraldehyde derived azetidine-2,3-diones by sequential Barbier-type addition reactions followed by hydroxy functionalization and aldehyde unmasking. The reaction between the above β-lactam aldehydes and 2-(trimethylsilyl)thiazole (TMST) gave as major products

  起始底物，对映体纯螺环或 3-取代 3-烷氧基-4-氧代氮杂环丁烷-2-甲醛，由 (R)-2,3-O-异丙基甘油醛衍生的氮杂环丁烷-2,3-二酮通过顺序巴比耶型加成反应制备然后是羟基官能化和醛暴露。上述 β-内酰胺醛与 2-(三甲基甲硅烷基)噻唑 (TMST) 之间的反应产生构象受限的 α-烷氧基-γ-酮酰胺作为主要产物，其既可以被认为是醛醇，也可以被认为是 Passerini 型产物，通过N1–C4 β-内酰胺键断裂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)