6',7'-Dichloro-1',2'-dihydrospiro([1,3]dioxane-2,3'-indole)-2'-one | 883647-79-8

• 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: 6',7'-Dichloro-1',2'-dihydrospiro([1,3]dioxane-2,3'-indole)-2'-one
• 英文别名: 6',7'-dichlorospiro[1,3-dioxane-2,3'-1H-indole]-2'-one
• CAS: 883647-79-8
• 化学式: C₁₁H₉Cl₂NO₃
• mdl: MFCD07441771
• 分子量: 274.103
• InChiKey: HXLXZVWHEKENSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 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：

  6',7'-Dichloro-1',2'-dihydrospiro([1,3]dioxane-2,3'-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 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-((6,7-dichlorospiro[indole-3,2'-[1,3]dioxan]-2-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 (2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(6,7-dichloro-2-oxospiro[indoline-3,2'-[1,3]dioxan]-1-yl)tetrahydro-2H-pyran-3,4-diyl diacetate
  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.