4-(azidomethyl)-2-(3-chlorophenyl)-1,3-dioxolane | 1015479-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(azidomethyl)-2-(3-chlorophenyl)-1,3-dioxolane
• 英文别名: 4-(Azidomethyl)-2-(3-chlorophenyl)-1,3-dioxolane
• CAS: 1015479-90-9
• 化学式: C₁₀H₁₀ClN₃O₂
• 分子量: 239.661
• InChiKey: OAJXTNRPIYVSGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 4-(azidomethyl)-2-(3-chlorophenyl)-1,3-dioxolane 在 三氟化硼乙醚 、 甲醇 作用下， 以 硝基甲烷 为溶剂， 反应 12.25h， 以74%的产率得到cis-[8-(3-chloro-phenyl)-5,6-dihydro-8H-tetrazolo[5,1-c][1,4]oxazin-6-yl]methanol
  参考文献：
  名称：

  Proximity-Assisted Cycloaddition ReactionsFacile Lewis Acid-Mediated Synthesis of Diversely Functionalized Bicyclic Tetrazoles

  摘要：

  Aliphatic azidonitriles separated by three or four carbon atoms undergo facile Lewis acid-induced cycloadditions to give bicyclic tetrazoles, even at 0 degrees C. Extension to 3-azido-2-aryl-1,3-dioxolanes and the corresponding 1,3-dioxanes in the presence of TMSCN and BF3 center dot OEt2 leads to a series of diversely functionalized novel oxabicyclic tetrazoles. The reactions represent new aspects of proximity-assisted dipolar cycloadditions that afford thermodynamically controlled enantiopure products proceeding through discrete oxocarbenium ion intermediates.

  DOI：

  10.1021/ol703071c
• 作为产物：
  描述：

  3-azidopropane-1,2-diol 、 3-氯苯甲醛 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以78%的产率得到4-(azidomethyl)-2-(3-chlorophenyl)-1,3-dioxolane
  参考文献：
  名称：

  Tetrazoles的还原性断裂：机理的见解和对2，6-聚取代的吗啉的立体控制合成的应用。

  摘要：

  描述了一种在温和条件下通过还原二氧杂环四唑合成2,6-二-和2,2'，6-三取代的吗啉的新方法。事实证明，该反应可用于多种四唑，包括在叔碳中心上带有宝石取代基的空间受限四唑。阐明了将数十年来四唑还原为仲胺的机理。

  DOI：

  10.1021/acs.orglett.9b01842

文献信息

• Reductive Fragmentation of Tetrazoles: Mechanistic Insights and Applications toward the Stereocontrolled Synthesis of 2,6-Polysubstituted Morpholines
  作者：Edouard Duchamp、Benoit Deschênes Simard、Stephen Hanessian

  DOI：10.1021/acs.orglett.9b01842

  日期：2019.9.6

  synthesize 2,6-di-, and 2,2',6-trisubstituted morpholines via the reduction of oxabicyclic tetrazoles under mild conditions is described. The reaction proved successful for a wide range of tetrazoles, including sterically encumbered ones harboring gem-substituents on tertiary carbon centers. The mechanism for the decades-old reduction of tetrazoles to secondary amines is elucidated.

  描述了一种在温和条件下通过还原二氧杂环四唑合成2,6-二-和2,2'，6-三取代的吗啉的新方法。事实证明，该反应可用于多种四唑，包括在叔碳中心上带有宝石取代基的空间受限四唑。阐明了将数十年来四唑还原为仲胺的机理。
• Proximity-Assisted Cycloaddition ReactionsFacile Lewis Acid-Mediated Synthesis of Diversely Functionalized Bicyclic Tetrazoles
  作者：Stephen Hanessian、Daniel Simard、Benoît Deschênes-Simard、Caroline Chenel、Edgar Haak

  DOI：10.1021/ol703071c

  日期：2008.4.1

  Aliphatic azidonitriles separated by three or four carbon atoms undergo facile Lewis acid-induced cycloadditions to give bicyclic tetrazoles, even at 0 degrees C. Extension to 3-azido-2-aryl-1,3-dioxolanes and the corresponding 1,3-dioxanes in the presence of TMSCN and BF3 center dot OEt2 leads to a series of diversely functionalized novel oxabicyclic tetrazoles. The reactions represent new aspects of proximity-assisted dipolar cycloadditions that afford thermodynamically controlled enantiopure products proceeding through discrete oxocarbenium ion intermediates.