(-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-2-azetidinone | 276244-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-2-azetidinone
• CAS: 276244-17-8
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: JZMBWWZILIADDJ-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-2-azetidinone 在 甲醇 、 sodium methylate 作用下， 反应 0.33h， 以95%的产率得到(+)-(3R,4R)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-pentynyl)-2-azetidinone
  参考文献：
  名称：

  Regio- and Stereocontrolled Metal-Mediated Carbonyl Propargylation or Allenylation of Enantiomerically Pure Azetidine-2,3-diones:  Synthesis of Highly Functionalized 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Regio and stereocontrolled metal-mediated Barbier-type reactions of azetidine-2,3-diones with differently substituted propargyl bromides offer an efficient asymmetric entry to densely functionalized 3-propargyl- (or allenyl-) substituted 3-hydroxy-beta-lactams.

  DOI：

  10.1021/ol005736f
• 作为产物：
  描述：

  N-(4-pentynyl)-2,3-O-(isopropylidene)-D-glyceraldehyde imine 、 乙酰氧基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以65%的产率得到(-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-pentynyl)-2-azetidinone
  参考文献：
  名称：

  Regio- and Stereocontrolled Metal-Mediated Carbonyl Propargylation or Allenylation of Enantiomerically Pure Azetidine-2,3-diones:  Synthesis of Highly Functionalized 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Regio and stereocontrolled metal-mediated Barbier-type reactions of azetidine-2,3-diones with differently substituted propargyl bromides offer an efficient asymmetric entry to densely functionalized 3-propargyl- (or allenyl-) substituted 3-hydroxy-beta-lactams.

  DOI：

  10.1021/ol005736f

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.