(6S,7R,8S)-7-(4-bromophenyl)-4-((2-nitrophenyl)sulfonyl)-8-((trityloxy)methyl)-1,4-diazabicyclo[4.2.0]octan-2-one | 1393810-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (6S,7R,8S)-7-(4-bromophenyl)-4-((2-nitrophenyl)sulfonyl)-8-((trityloxy)methyl)-1,4-diazabicyclo[4.2.0]octan-2-one
• 英文别名: (6S,7R,8S)-7-(4-bromophenyl)-8-(hydroxymethyl)-4-(2-nitrophenyl)sulfonyl-1,4-diazabicyclo[4.2.0]octan-2-one
• CAS: 1393810-12-2
• 化学式: C₁₉H₁₈BrN₃O₆S
• 分子量: 496.338
• InChiKey: WHHVAERXAOVPDV-GPMSIDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6S,7R,8S)-7-(4-bromophenyl)-4-((2-nitrophenyl)sulfonyl)-8-((trityloxy)methyl)-1,4-diazabicyclo[4.2.0]octan-2-one 在 氟化氢吡啶 、 甲氧基三甲基硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [(2R,3S)-2-(hydroxymethyl)-3-phenyl-1-(pyridine-3-carbonyl)-1,6-diazaspiro[3.3]heptan-6-yl]-pyridin-3-ylmethanone
  参考文献：
  名称：

  Synthesis and Profiling of a Diverse Collection of Azetidine-Based Scaffolds for the Development of CNS-Focused Lead-like Libraries

  摘要：

  The synthesis and diversification of a densely functionalized azetidine ring system to gain access to a wide variety of fused, bridged, and spirocyclic ring systems is described. The in vitro physicochemical and pharmacokinetic properties of representative library members are measured in order to evaluate the use of these scaffolds for the generation of lead-like molecules to be used in targeting the central nervous system. The solid-phase synthesis of a 1976-membered library of spirocyclic azetidines is also described.

  DOI：

  10.1021/jo300974j
• 作为产物：
  描述：

  在 三乙基硅烷 、 caesium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.75h， 生成 (6S,7R,8S)-7-(4-bromophenyl)-4-((2-nitrophenyl)sulfonyl)-8-((trityloxy)methyl)-1,4-diazabicyclo[4.2.0]octan-2-one
  参考文献：
  名称：

  Synthesis and Profiling of a Diverse Collection of Azetidine-Based Scaffolds for the Development of CNS-Focused Lead-like Libraries

  摘要：

  The synthesis and diversification of a densely functionalized azetidine ring system to gain access to a wide variety of fused, bridged, and spirocyclic ring systems is described. The in vitro physicochemical and pharmacokinetic properties of representative library members are measured in order to evaluate the use of these scaffolds for the generation of lead-like molecules to be used in targeting the central nervous system. The solid-phase synthesis of a 1976-membered library of spirocyclic azetidines is also described.

  DOI：

  10.1021/jo300974j

文献信息

• Synthesis and Profiling of a Diverse Collection of Azetidine-Based Scaffolds for the Development of CNS-Focused Lead-like Libraries
  作者：Jason T. Lowe、Maurice D. Lee、Lakshmi B. Akella、Emeline Davoine、Etienne J. Donckele、Landon Durak、Jeremy R. Duvall、Baudouin Gerard、Edward B. Holson、Adrien Joliton、Sarathy Kesavan、Berenice C. Lemercier、Haibo Liu、Jean-Charles Marié、Carol A. Mulrooney、Giovanni Muncipinto、Morgan Welzel-O’Shea、Laura M. Panko、Ann Rowley、Byung-Chul Suh、Meryl Thomas、Florence F. Wagner、Jingqiang Wei、Michael A. Foley、Lisa A. Marcaurelle

  DOI：10.1021/jo300974j

  日期：2012.9.7

  The synthesis and diversification of a densely functionalized azetidine ring system to gain access to a wide variety of fused, bridged, and spirocyclic ring systems is described. The in vitro physicochemical and pharmacokinetic properties of representative library members are measured in order to evaluate the use of these scaffolds for the generation of lead-like molecules to be used in targeting the central nervous system. The solid-phase synthesis of a 1976-membered library of spirocyclic azetidines is also described.