(1E)-2-azido-3,5-O-benzylidene-1,2-dideoxy-1-fluoro-4-O-formyl-D-erythro-pent-1-enitol | 1028191-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (1E)-2-azido-3,5-O-benzylidene-1,2-dideoxy-1-fluoro-4-O-formyl-D-erythro-pent-1-enitol
• 英文别名: [(2R,4S,5R)-4-[(E)-1-azido-2-fluoroethenyl]-2-phenyl-1,3-dioxan-5-yl] formate
• CAS: 1028191-96-9
• 化学式: C₁₃H₁₂FN₃O₄
• 分子量: 293.254
• InChiKey: XCYYZMKBDPFSFQ-GAANKIBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1E)-2-azido-3,5-O-benzylidene-1,2-dideoxy-1-fluoro-4-O-formyl-D-erythro-pent-1-enitol 以 苯 为溶剂， 反应 1.0h， 以98%的产率得到3-(D-erythro-1,3-O-benzylidene-2-O-formyl-propyl)-2-fluoro-2H-azirine
  参考文献：
  名称：

  Synthesis of Polyhydroxylated 2H-Azirines and 2-Halo-2H-azirines from 3-Azido-2,3-dideoxyhexopyranoses by Alkoxyl Radical Fragmentation

  摘要：

  The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.

  DOI：

  10.1021/jo800182y
• 作为产物：
  描述：

  2-azido-3,5-O-benzylidene-1,2-dideoxy-1-fluoro-4-O-formyl-1-iodo-D-arabinitol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 1.0h， 以33%的产率得到(1E)-2-azido-3,5-O-benzylidene-1,2-dideoxy-1-fluoro-4-O-formyl-D-erythro-pent-1-enitol
  参考文献：
  名称：

  Synthesis of Polyhydroxylated 2H-Azirines and 2-Halo-2H-azirines from 3-Azido-2,3-dideoxyhexopyranoses by Alkoxyl Radical Fragmentation

  摘要：

  The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.

  DOI：

  10.1021/jo800182y