(-)-(3R,4R)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(2-propynyl)-2-azetidinone | 358973-80-5

• 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,4R)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(2-propynyl)-2-azetidinone
• 英文别名: (3R,4S)-3-hydroxy-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-N-(2-propynyl)-2-azetidinone；(3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-prop-2-ynylazetidin-2-one
• CAS: 358973-80-5
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: OSOVUWHPSKZQFJ-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (-)-(3R,4R)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(2-propynyl)-2-azetidinone 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(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-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
• 作为产物：
  描述：

  (-)-(3R,4S)-3-acetoxy-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(2-propynyl)-2-azetidinone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以94%的产率得到(-)-(3R,4R)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(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

文献信息

• Gold-catalyzed bis-cyclization of 1,2-diol- or acetonide-tethered alkynes. Synthesis of ?-lactam-bridged acetals: a combined experimental and theoretical study
  作者：Benito Alcaide、Pedro Almendros、Roco Carrascosa、Ramn Lpez、Mara I. Menndez

  DOI：10.1016/j.tet.2012.03.028

  日期：2012.12

  alkyn-1,2-diols or alkynyl acetonides, readily prepared from imines of (R)-2,3-O-isopropylideneglyceraldehyde, were used as starting materials for the regio- and diastereospecific catalytic bis-oxycyclization reaction in the presence of a gold/acid binary system. Interestingly, in contrast to the gold-catalyzed reactions of N-tethered terminal alkynes, which lead to the corresponding 6,8-dioxabicyclo[3

  由（R）-2,3- O-异亚丙基甘油醛的亚胺容易制得的2-氮杂环丁酮系链的炔基1,2-二醇或炔基丙酮化物被用作原料的区域和非对映异构催化双氧环化反应的起始原料金/酸二元体系的存在。有趣的是，与N系链末端炔烃的金催化反应（其生成相应的6,8-二氧杂双环[3.2.1]辛烷衍生物（近端加合物））相反，在相同条件下，取代的炔二醇和丙酮化物的反应通过独家的7- end / 5- exo生成7,9-dioxabicyclocyclo [4.2.1] nonane衍生物（远端加合物）作为唯一产品通过氧原子最初攻击外部炔烃碳而进行双-氧环化。而且，该方法的温和性允许掺入1，3-二炔部分作为反应性伴侣，对内部的炔基部分表现出优异的化学选择性。为了确认该机械方案，已经进行了使用氘化氘的标记研究。此外，进行密度泛函计算以深入了解双氧环化反应的机理。
• 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
  作者：Benito Alcaide、Pedro Almendros、Raquel Rodríguez-Acebes

  DOI：10.1021/jo016247b

  日期：2002.3.1

  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.