(3S,4R)-4-(3-phenyl-2-propynyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone | 119979-53-2

• 英文名称: (3S,4R)-4-(3-phenyl-2-propynyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
• 英文别名: (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-(3-phenylprop-2-ynyl)azetidin-2-one
• CAS: 119979-53-2
• 化学式: C₂₀H₂₉NO₂Si
• 分子量: 343.541
• InChiKey: VGRDFLKDXYGINB-KBAYOESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-(3-phenyl-2-propynyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 以30%的产率得到(5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-2-phenyl-1-azabicyclo[3.2.0]hept-3-en-7-one
  参考文献：
  名称：

  Synthesis of 4-allenyl and 4-proparyl-2-azetidinone via Zn-mediated Barbier-type reaction and Pt-catalyzed intramolecular amidation to carbapenem skeletons

  摘要：

  4-Propargyl-2-azetidinone and 4-allenyl-2-azetidinone derivatives can be facilely obtained from 4-acetoxy-2-azetidinone and propargyl bromides via zinc-mediated Barbier-type reaction. A new method has been developed to construct the carbapenem bicyclic nucleus by cyclization of 4-propargyl-2-azetidinone and 4-allenyl-2-azetidinone derivatives catalyzed by PtCl2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.061
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4R)-4-(3-phenyl-2-propynyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone
  参考文献：
  名称：

  Silver Mediated Cyclizations of 4-Allenyl-and 4-(2-Propynyl)azetidinones. A Stereoselective Synthesis of 3-Substituted Δ1-Carbapenems Via N-C3 Closure.

  摘要：

  DOI：

  10.1016/s0040-4039(00)80467-0

文献信息

• Palladium Mediated Formation of Δ1- and Δ2-Carbapenems by Cyclofunctionalization of 4-Allenylazetidinones and 4-(2-Propynyl)azetidinones.
  作者：J. Siva Prasad、Lanny S. Liebeskind

  DOI：10.1016/s0040-4039(00)80468-2

  日期：1988.1
• Synthesis of 3-Selena-1-dethiacephems and Selenazepines via Iodocyclization
  作者：Dinesh R. Garud、Mamoru Koketsu

  DOI：10.1021/ol801010y

  日期：2008.8.7

  A convenient approach to synthesize novel selenium-beta-lactams, 3-selena-1-dethiacephems and selenazepines, was accomplished via the regioselective iodocyclization reaction. The substituent of allenyl moieties dramatically influenced the regiochemical outcome in the iodocyclization of allene-selenourea derivatives.