(2R,3S,4S)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile | 1393809-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,4S)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile
• 英文别名: (2S,3S,4R)-3-(4-bromophenyl)-1-prop-2-enyl-4-(trityloxymethyl)azetidine-2-carbonitrile
• CAS: 1393809-87-4
• 化学式: C₃₃H₂₉BrN₂O
• 分子量: 549.51
• InChiKey: OXPKMQJBKUIYSR-RTOKGZNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile 在 LiTMP 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 15.67h， 生成 (2R,3R)-1-allyl-2-(hydroxymethyl)-3-(para-bromophenyl)-6-(ortho-nosyl)-1,6-diazaspiro[3.3]heptane
  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：

  2-[[(1S,2S)-1-(4-bromophenyl)-1-chloro-3-trityloxypropan-2-yl]-prop-2-enylamino]acetonitrile 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以40%的产率得到(2R,3S,4S)-1-allyl-3-(4-bromophenyl)-2-(trityloxymethyl)azetidine-4-carbonitrile
  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