4'-chlorospiro[1,3-dioxane-2,3'-1H-indole]-2'-one | 1092300-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4'-chlorospiro[1,3-dioxane-2,3'-1H-indole]-2'-one
• CAS: 1092300-55-4
• 化学式: C₁₁H₁₀ClNO₃
• 分子量: 239.658
• InChiKey: VVZWYPFQWYXDOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-chlorospiro[1,3-dioxane-2,3'-1H-indole]-2'-one 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 15-冠醚-5 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以18%的产率得到N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,3-(trimethylenedioxy)-4-chloroindolin-2-one
  参考文献：
  名称：

  Synthesis of heteroaromatic N-β-glycosides of N-acetylglucosamine under phase transfer conditions: II. Indolin-2-one glycosaminides

  摘要：

  Regioselective N-beta-glucosamination of various unsubstituted or C4-, C5-, or C6-monosubstituted indolin-2-ones under phase transfer conditions was studied. The regioselectivity was unambiguously proved by H-1 NMR spectroscopy and X-ray analysis. The presence of substituent at C7 of the aromatic ring leads to the formation of either a mixture of isomeric N-beta- and O-beta-D-glucosaminides, or only oxazoline and/or 2-acetamidoglycal irrespective of the reaction conditions.

  DOI：

  10.1134/s1068162008060137

文献信息

• Synthesis of heteroaromatic N-β-glycosides of N-acetylglucosamine under phase transfer conditions: II. Indolin-2-one glycosaminides
  作者：V. O. Kur’yanov、T. A. Chupakhina、O. V. Shishkin、S. V. Shishkina、V. Ya. Chirva

  DOI：10.1134/s1068162008060137

  日期：2008.11

  Regioselective N-beta-glucosamination of various unsubstituted or C4-, C5-, or C6-monosubstituted indolin-2-ones under phase transfer conditions was studied. The regioselectivity was unambiguously proved by H-1 NMR spectroscopy and X-ray analysis. The presence of substituent at C7 of the aromatic ring leads to the formation of either a mixture of isomeric N-beta- and O-beta-D-glucosaminides, or only oxazoline and/or 2-acetamidoglycal irrespective of the reaction conditions.