6-甲基-2,3-二氢-苯并呋喃-2-羧酸 | 26018-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 6-甲基-2,3-二氢-苯并呋喃-2-羧酸
• 英文名称: 6-Methyl-2,3-dihydrobenzofuran-2-carboxylic acid
• 英文别名: 6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid
• CAS: 26018-42-8
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: OALGDQAPRDHTMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-甲基-2,3-二氢-苯并呋喃-2-羧酸 在 氯化亚砜 、 氨 、 sodium methylate 、 phosphorus pentoxide 作用下， 以 1,4-二氧六环 、 甲苯 、 苯 为溶剂， 反应 8.75h， 生成 2-(6-methyl-2,3-dihydrobenzofuran-2-yl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003
• 作为产物：
  描述：

  6-甲基-苯并呋喃-2-羧酸 在 sodium amalgam 作用下， 以 sodium hydroxide 为溶剂， 反应 2.5h， 生成 6-甲基-2,3-二氢-苯并呋喃-2-羧酸
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003

文献信息

• US4085117A
  申请人：——

  公开号：US4085117A

  公开（公告）日：1978-04-18
• US4087542A
  申请人：——

  公开号：US4087542A

  公开（公告）日：1978-05-02
• US4100294A
  申请人：——

  公开号：US4100294A

  公开（公告）日：1978-07-11
• US4163794A
  申请人：——

  公开号：US4163794A

  公开（公告）日：1979-08-07
• US4181727A
  申请人：——

  公开号：US4181727A

  公开（公告）日：1980-01-01