(3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one | 358973-69-0

• 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,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one
• 英文别名: (3R,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)-3-(2-methylbut-3-en-2-yl)azetidin-2-one
• CAS: 358973-69-0
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: JSIDEMAAEGBMSM-GQIGUUNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  硫酸二甲酯 、 (3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one 在 sodium hydroxide 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到(3R,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methoxy-1-(4-methoxyphenyl)-3-(2-methylbut-3-en-2-yl)azetidin-2-one
  参考文献：
  名称：

  N1–C4 β-内酰胺键在 2-（三甲基甲硅烷基）噻唑加成到 β-内酰胺醛中：螺旋和叔α-烷氧基-γ-酮酸衍生物的不对称合成

  摘要：

  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)

  DOI：

  10.1002/ejoc.200700231
• 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 、 氯化铵 、 二甲基亚砜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one
  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

• 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
  作者：Benito Alcaide、Pedro Almendros、Cristina Aragoncillo、Raquel Rodríguez-Acebes

  DOI：10.1021/jo015704l

  日期：2001.7.1

  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.
• 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)