(-)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(2-propenyl)-3-(2-propynyl)-2-azetidinone | 276244-11-2

• 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-dioxolan-4-yl]-3-hydroxy-1-(2-propenyl)-3-(2-propynyl)-2-azetidinone
• 英文别名: (3R,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-prop-2-enyl-3-prop-2-ynylazetidin-2-one
• CAS: 276244-11-2
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: PHIKLQUCCZEIFA-UHIISALHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴丙炔 、 (-)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(2-propenyl)-3-(2-propynyl)-2-azetidinone 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 以56%的产率得到(-)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(2-propynyl)-3-(2-propynyl)-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：

  (-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propenyl)-2-azetidinone 在 草酰氯 、 sodium methylate 、 氯化铵 、 二甲基亚砜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 (-)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(2-propenyl)-3-(2-propynyl)-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