(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone | 220574-31-2

• 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)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone
• 英文别名: (3R,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)-3-prop-2-enylazetidin-2-one
• CAS: 220574-31-2
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: WKJHGHLZXNWWNF-RVKKMQEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone 在 Grubbs catalyst first generation 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (1S,4R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(4-methoxyphenyl)-5-oxa-2-azaspiro[3.4]oct-6-en-3-one
  参考文献：
  名称：

  通过Barbier型反应，然后通过金属催化的环化反应，从α-氧代-β-内酰胺以多样性为导向的对映纯螺环2-氮杂环丁酮类化合物的制备

  摘要：

  通过使用不同的金属介导的羰基加成/环化反应序列，已经开发出新颖，简单和方便的策略来实现多种功能化的螺环β-内酰胺。螺环化前体，2-氮杂环丁酮拴系的均烯丙基醇，溴代均烯丙基醇，均丙炔醇，（buta-1,3-dien-2-yl）甲醇和α-烯醇是通过将稳定的有机金属试剂区域选择性地添加到氮杂环丁烷2中而获得的，3-二酮在水性环境中。上述单环不饱和醇衍生物的钌，银和钯催化的反应提供了oxaspiro-β-内酰胺。

  DOI：

  10.1002/adsc.200600502
• 作为产物：
  描述：

  (3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one 在 草酰氯 、 四氯化锡 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone
  参考文献：
  名称：

  Metal-Promoted Allylation, Propargylation, or Allenylation of Azetidine-2,3-diones in Aqueous and Anhydrous Media. Application to the Asymmetric Synthesis of Densely Functionalized 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Metal-mediated carbonyl allylation, allenylation, and propargylation of optically pure azetidine-2,3-diones were investigated in both anhydrous and aqueous environments. Different metals promoters showed varied regioselectivities on product formation during allenylation/propargylation reactions of the keto-beta -lactams. The stereochemistry of the new C3-substituted C3-hydroxy quaternary center was controlled by placing a chiral auxiliary at C4. In this way, the coupling of azetidine-2,3-diones with a variety of propenyl-, propynyl-, and allenylmetal reagents offers a convenient asymmetric entry to potentially bioactive 3-substituted 3-hydroxy-beta -lactams.

  DOI：

  10.1021/jo015704l

文献信息

• 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)
• New Aspects of the Indium Chemistryof Carbonyl-β-lactams
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo、Raquel Rodríguez-Acebes

  DOI：10.1055/s-2003-39388

  日期：——

  Reactions of racemic as well as optically pure carbonyl-β-lactams with stabilized organo-indium reagents were investigated in aqueous media. The regio- and stereochemistry of the processes were generally good, offering a convenient asymmetric entry to densely functionalized hydroxy-β-lactams.

  研究了外消旋和光学纯羰基-δ-内酰胺与稳定的有机铟试剂在水介质中的反应。反应过程的区域和立体化学性质普遍良好，为获得官能化程度较高的羟基δ-内酰胺提供了便捷的不对称途径。
• Asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-β-lactams via novel, highly stereoselective Baylis-Hillman and allylation reactions of enantiopure 3-oxo-2-azetidinones
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo

  DOI：10.1016/s0040-4039(99)01527-0

  日期：1999.10

  New asymmetric routes based on both Baylis-Hillman and allylation reactions of enantiopure 3-oxo-2-azetidinones are used for the highly stereoselective, efficient preparation of densely functionalized 3-substituted 3-hydroxy-beta-lactams. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Metal-assisted synthesis of enantiopure spirocyclic β-lactams from azetidine-2,3-diones
  作者：Benito Alcaide、Pedro Almendros、Teresa Martı́nez-del Campo、Raquel Rodrı́guez-Acebes

  DOI：10.1016/j.tetlet.2004.06.130

  日期：2004.8

  A novel approach to enantiopure spirocyclic beta-lactams has been developed by using different intramolecular metal-catalyzed cyclization reactions in monocyclic unsaturated alcohols. The access to cyclization precursors, 2-azetidinone-tethered homoallylic alcohols, (buta-1,3-dien2-yl)methanols, and alpha-allenols was achieved by regio and stereoselective addition of stabilized organo-indium reagents to azetidine-2,3-diones in aqueous environment. (C) 2004 Elsevier Ltd. All rights reserved.