2-iodo-5-nitro-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)benzamide | 1408314-32-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-iodo-5-nitro-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)benzamide
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2-iodo-5-nitrobenzoyl)amino]oxan-2-yl]methyl acetate
• CAS: 1408314-32-8
• 化学式: C₂₁H₂₃IN₂O₁₂
• 分子量: 622.324
• InChiKey: LWHMLTXWYVYDTA-WVXKDWSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)acetylene 、 2-iodo-5-nitro-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)benzamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以81%的产率得到[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[2-[2-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethynyl]-5-nitrobenzoyl]amino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of Lactams

  摘要：

  The iodocyclization of o-allcynylbenzamides with various electrophiles has been reported to yield five- or six-membered lactams by nucleophilic attack of the amide nitrogen onto the triple bond. While the formation of an isobenzofuran-1(3H)-imine with two bulky substituents under Larock conditions was initially attributed to steric hindrance, we found out that cyclization via the amide oxygen is the rule rather than the exception. Thus, the structures of the products reported in the literature need to be revised.

  DOI：

  10.1021/jo3017378
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-BETA-D-吡喃半乳糖胺 、 2-iodo-5-nitrobenzoyl chloride 在 N-乙基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以87%的产率得到2-iodo-5-nitro-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)benzamide
  参考文献：
  名称：

  Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of Lactams

  摘要：

  The iodocyclization of o-allcynylbenzamides with various electrophiles has been reported to yield five- or six-membered lactams by nucleophilic attack of the amide nitrogen onto the triple bond. While the formation of an isobenzofuran-1(3H)-imine with two bulky substituents under Larock conditions was initially attributed to steric hindrance, we found out that cyclization via the amide oxygen is the rule rather than the exception. Thus, the structures of the products reported in the literature need to be revised.

  DOI：

  10.1021/jo3017378