(-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propynyl)-2-azetidinone | 358973-76-9

• 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-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propynyl)-2-azetidinone
• 英文别名: (3R,4S)-3-acetoxy-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(2-propynyl)-2-azetidinone；[(2S,3R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-oxo-1-prop-2-ynylazetidin-3-yl] acetate
• CAS: 358973-76-9
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: MQUWJFUMIUVJCR-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

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-(2-propynyl)-2-azetidinone 在 草酰氯 、 sodium methylate 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 (4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propynyl)-azetidine-2,3-dione
  参考文献：
  名称：

  Metal-Mediated Carbonyl-1,3-butadien-2-ylation by 1,4-Bis(methanesulfonyl)-2-butyne or 1,4-Dibromo-2-butyne in Aqueous Media:  Asymmetric Synthesis of 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methanesulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.

  DOI：

  10.1021/jo016247b
• 作为产物：
  描述：

  N-(2-propynyl)-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， 生成 (-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propynyl)-2-azetidinone
  参考文献：
  名称：

  Metal-Mediated Carbonyl-1,3-butadien-2-ylation by 1,4-Bis(methanesulfonyl)-2-butyne or 1,4-Dibromo-2-butyne in Aqueous Media:  Asymmetric Synthesis of 3-Substituted 3-Hydroxy-β-lactams

  摘要：

  Metal-mediated 1,3-butadien-2-ylation reactions between 1,4-dibromo-2-butyne or 1,4-bis(methanesulfonyl)-2-butyne and optically pure azetidine-2,3-diones were investigated in aqueous media, offering a convenient asymmetric entry to the potentially bioactive 3-substituted 3-hydroxy-beta-lactam moiety. The diastereoselectivity of the addition reaction was controlled by the bulky chiral auxiliary at C4. However, while the regioselectivity of the process was full, the chemical yield of the addition was a function of the nature of both the metal reagent and the system solvent as well. In addition, 2-azetidinone-tethered 1,3-butadienes can easily be transformed into other functionalities via Diels-Alder reaction.

  DOI：

  10.1021/jo016247b

文献信息

• Synthesis of Novel Bis(β-lactam)-1,3-diynes by Copper-Promoted Homo- or Cross-Coupling of Alkynyl-2-azetidinones
  作者：Benito Alcaide、Pedro Almendros、Rocío Carrascosa、Raquel Rodríguez-Acebes

  DOI：10.1002/ejoc.200701083

  日期：2008.3

  of various (β-lactam)acetylenes to afford C2-symmetrical bis(β-lactam)-1,3-diynes, whereas these 2-azetidinone-tethered alkynes underwent the Cadiot–Chodkiewicz cross-coupling reaction with different 2-azetidinone bromoalkynes to form a variety of unsymmetrical bis(β-lactam)diynes in good yields. In addition to their potential biological activity, the resulting enantiopure bis(β-lactam)-1,3-diynes

  Cu(OAc)2 与 K2CO3（一种固体碱而不是胺）的组合被证明是一种非常有效的系统，可促进各种（β-内酰胺）乙炔的均偶联，以提供 C2-对称双（β-内酰胺）- 1,3-二炔，而这些 2-氮杂环丁酮系链炔与不同的 2-氮杂环丁酮溴炔发生 Cadiot-Chodkiewicz 交叉偶联反应，以良好的产率形成各种不对称的双（β-内酰胺）二炔。除了潜在的生物活性外，所得的对映体纯双（β-内酰胺）-1,3-二炔还可转化为双（β-氨基酯）-1,3-二炔，可用作大环腔，如以及手性配体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• 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.