diethyl 7-chloro-2,3-dihydro-3-hydroxy-6-methoxybenzofuran-2,2-dicarboxylate | 90246-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: diethyl 7-chloro-2,3-dihydro-3-hydroxy-6-methoxybenzofuran-2,2-dicarboxylate
• 英文别名: diethyl 7-chloro-3-hydroxy-6-methoxy-3H-1-benzofuran-2,2-dicarboxylate
• CAS: 90246-71-2
• 化学式: C₁₅H₁₇ClO₇
• 分子量: 344.749
• InChiKey: WDFIFZVQGUXZGD-UHFFFAOYSA-N

物化性质

• 沸点：
  424.8±45.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 7-chloro-2,3-dihydro-3-hydroxy-6-methoxybenzofuran-2,2-dicarboxylate 在 palladium on activated charcoal 三氯化铝 、 硫酸 、 水 、 氢气 、 二甲基亚砜 、 lithium chloride 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 4.0h， 生成 ethyl 7-chloro-2,3-dihydro-6-hydroxy-5-propionylbenzofuran-2-carboxylate
  参考文献：
  名称：

  Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity

  摘要：

  A series of substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazoles was prepared and evaluated for their saluretic and uricosuric properties. Pharmacological evaluation of the title compounds was carried out in mice, rats, dogs, and monkeys. The diuretic/saluretic nature of these compounds was observed in all species, whereas the uricosuric activity was best seen in the Cebus monkey. Evaluation of the enantiomers of 8-chloro-3-(o-fluorophenyl)-5,6-dihydrofuro [3,2-f]-1,2-benzisoxazole-6-carboxylic acid (15k) revealed that only the (+) enantiomer (29) displayed diuretic and saluretic activity, whereas both enantiomers possessed uricosuric activity. X-ray analysis showed that the (-) enantiomer (30) possesses the 2R configuration.

  DOI：

  10.1021/jm00374a014
• 作为产物：
  描述：

  3-chloro-2,4-dimethoxybenzaldehyde 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 5.5h， 生成 diethyl 7-chloro-2,3-dihydro-3-hydroxy-6-methoxybenzofuran-2,2-dicarboxylate
  参考文献：
  名称：

  Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity

  摘要：

  A series of substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazoles was prepared and evaluated for their saluretic and uricosuric properties. Pharmacological evaluation of the title compounds was carried out in mice, rats, dogs, and monkeys. The diuretic/saluretic nature of these compounds was observed in all species, whereas the uricosuric activity was best seen in the Cebus monkey. Evaluation of the enantiomers of 8-chloro-3-(o-fluorophenyl)-5,6-dihydrofuro [3,2-f]-1,2-benzisoxazole-6-carboxylic acid (15k) revealed that only the (+) enantiomer (29) displayed diuretic and saluretic activity, whereas both enantiomers possessed uricosuric activity. X-ray analysis showed that the (-) enantiomer (30) possesses the 2R configuration.

  DOI：

  10.1021/jm00374a014

文献信息

• Benzisoxazole carboxylic acids
  申请人：Abbott Laboratories

  公开号：US04456612A1

  公开（公告）日：1984-06-26

  Described are compounds of the formula ##STR1## wherein X is hydrogen, loweralkyl, halo, loweralkoxy or trifluoromethyl, and Z is hydrogen, loweralkyl, halo, hydroxy or alkoxy, or compounds of the formula ##STR2## wherein X' and Y' may be the same or different and are selected from hydrogen, loweralkyl, or halo, and Z' is hydrogen, loweralkyl, halo, hydroxy or loweralkoxy, or pharmaceutically acceptable salts thereof. The compounds possess diuretic activity.

  描述的化合物公式为##STR1##其中X是氢、较低烷基、卤素、较低烷氧基或三氟甲基，Z是氢、较低烷基、卤素、羟基或烷氧基，或者公式为##STR2##的化合物，其中X'和Y'可以相同也可以不同，选择自氢、较低烷基或卤素，Z'是氢、较低烷基、卤素、羟基或较低烷氧基，或其药用可接受盐。这些化合物具有利尿活性。
• J. Med. Chem. 1984, 27, 1016-1026
  作者：

  DOI：——

  日期：——
• US4456612A
  申请人：——

  公开号：US4456612A

  公开（公告）日：1984-06-26
• US4490384A
  申请人：——

  公开号：US4490384A

  公开（公告）日：1984-12-25
• Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity
  作者：Jacob J. Plattner、Anthony K. L. Fung、James A. Parks、Richard J. Pariza、Steven R. Crowley、Andre G. Pernet、Paul R. Bunnell、Patrick W. Dodge

  DOI：10.1021/jm00374a014

  日期：1984.8

  A series of substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazoles was prepared and evaluated for their saluretic and uricosuric properties. Pharmacological evaluation of the title compounds was carried out in mice, rats, dogs, and monkeys. The diuretic/saluretic nature of these compounds was observed in all species, whereas the uricosuric activity was best seen in the Cebus monkey. Evaluation of the enantiomers of 8-chloro-3-(o-fluorophenyl)-5,6-dihydrofuro [3,2-f]-1,2-benzisoxazole-6-carboxylic acid (15k) revealed that only the (+) enantiomer (29) displayed diuretic and saluretic activity, whereas both enantiomers possessed uricosuric activity. X-ray analysis showed that the (-) enantiomer (30) possesses the 2R configuration.