N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-iodobenzamide | 693810-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-iodobenzamide
• CAS: 693810-52-5
• 化学式: C₂₁H₂₂INO₆
• 分子量: 511.313
• InChiKey: VOEHQNBCCRDNOA-CBUBUMAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-iodobenzamide 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 methyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-(2-iodobenzoylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  A new 20-membered macrocyclic dilactam: an unexpected product of a tri-n-butyltin hydride-mediated radical reaction

  摘要：

  The tri-n-butyltin hydride-mediated reaction of methyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-(2-iodobenzoylamino)-alpha-D-glucopyranoside affords an unexpected benzomacrodilactam. The structure of this new 20-membered macrocyclic dilactam has been elucidated by electrospray mass and tandem mass spectrometry (ESI-MS/MS) and by H-1, C-13 NMR spectroscopy, COSY, TOCSY, HMQC and HMBC experiments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.116
• 作为产物：
  描述：

  在 IR-120 resin 、 zinc(II) chloride 作用下， 生成 N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-iodobenzamide
  参考文献：
  名称：

  A new 20-membered macrocyclic dilactam: an unexpected product of a tri-n-butyltin hydride-mediated radical reaction

  摘要：

  The tri-n-butyltin hydride-mediated reaction of methyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-(2-iodobenzoylamino)-alpha-D-glucopyranoside affords an unexpected benzomacrodilactam. The structure of this new 20-membered macrocyclic dilactam has been elucidated by electrospray mass and tandem mass spectrometry (ESI-MS/MS) and by H-1, C-13 NMR spectroscopy, COSY, TOCSY, HMQC and HMBC experiments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.116