8-Bromo-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid | 1152567-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-Bromo-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid
• 英文别名: 5-bromo-2,3-dihydro-1,4-benzodioxine-7-carboxylic acid
• CAS: 1152567-51-5
• 化学式: C₉H₇BrO₄
• mdl: MFCD11103515
• 分子量: 259.056
• InChiKey: XITHRQNLVXVDRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-Bromo-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 三甲基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 54.0h， 以89%的产率得到(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(8-bromo-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis and glycogen phosphorylase inhibitory activity of N-(β-d-glucopyranosyl)amides possessing 1,4-benzodioxane moiety

  摘要：

  A series of N-(beta-D-glucopyranosyl)amides 5d-i were synthesized by PMe3 mediated Staudinger reaction of O-peracetylated beta-D-glucopyranosyl azide (1) followed by acylation with carboxylic acids 3d-i and subsequent Zemplen deacetylation. The new compounds were tested for their inhibitory activity against rabbit muscle glycogen phosphorylase and the structure-activity relationships of these compounds are also discussed in this paper. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.052
• 作为产物：
  描述：

  8-溴-2,3-二氢苯并[b][1,4]二噁英-6-甲醛 在 potassium permanganate 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 以73%的产率得到8-Bromo-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and glycogen phosphorylase inhibitory activity of N-(β-d-glucopyranosyl)amides possessing 1,4-benzodioxane moiety

  摘要：

  A series of N-(beta-D-glucopyranosyl)amides 5d-i were synthesized by PMe3 mediated Staudinger reaction of O-peracetylated beta-D-glucopyranosyl azide (1) followed by acylation with carboxylic acids 3d-i and subsequent Zemplen deacetylation. The new compounds were tested for their inhibitory activity against rabbit muscle glycogen phosphorylase and the structure-activity relationships of these compounds are also discussed in this paper. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.052

文献信息

• Synthesis and glycogen phosphorylase inhibitory activity of N-(β-d-glucopyranosyl)amides possessing 1,4-benzodioxane moiety
  作者：Zoltán Czakó、László Juhász、Ágnes Kenéz、Katalin Czifrák、László Somsák、Tibor Docsa、Pál Gergely、Sándor Antus

  DOI：10.1016/j.bmc.2009.07.052

  日期：2009.9

  A series of N-(beta-D-glucopyranosyl)amides 5d-i were synthesized by PMe3 mediated Staudinger reaction of O-peracetylated beta-D-glucopyranosyl azide (1) followed by acylation with carboxylic acids 3d-i and subsequent Zemplen deacetylation. The new compounds were tested for their inhibitory activity against rabbit muscle glycogen phosphorylase and the structure-activity relationships of these compounds are also discussed in this paper. (C) 2009 Elsevier Ltd. All rights reserved.