5-氟-2,3-二氢苯并呋喃-7-醇 | 245762-37-2

• 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: 5-氟-2,3-二氢苯并呋喃-7-醇
• 英文名称: 5-fluoro-7-hydroxy-2,3-dihydrobenzofuran
• 英文别名: 5-Fluoro-2,3-dihydrobenzofuran-7-ol；5-fluoro-2,3-dihydro-1-benzofuran-7-ol
• CAS: 245762-37-2
• 化学式: C₈H₇FO₂
• mdl: MFCD08236759
• 分子量: 154.141
• InChiKey: FRNAZUFNLWZOKK-UHFFFAOYSA-N

物化性质

• 熔点：
  102.5-103.5 °C
• 沸点：
  262.3±40.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟-2,3-二氢苯并呋喃-7-醇 在 sodium azide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 48.0h， 生成 2-(5-fluoro-2,3-dihydrobenzofuran-7-yloxy)ethyl azide
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010
• 作为产物：
  描述：

  5-氟-2,3-二氢苯并[b]呋喃 在 4,4'-硫联二(6-叔丁基-2-甲基苯酚) 、 四氯化钛 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 5-氟-2,3-二氢苯并呋喃-7-醇
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010

文献信息

• N-ARYLOXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
  申请人：Wyeth

  公开号：EP1068184B1

  公开（公告）日：2002-09-04
• N-ARYLOXYETHYL-INDOLY-ALKYLAMINES FOR THE TREATMENT OF DEPRESSION (5-HT1A RECEPTOR ACTIVE AGENTS)
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1070050A1

  公开（公告）日：2001-01-24
• US6121307A
  申请人：——

  公开号：US6121307A

  公开（公告）日：2000-09-19
• US6110956A
  申请人：——

  公开号：US6110956A

  公开（公告）日：2000-08-29
• US6291683B1
  申请人：——

  公开号：US6291683B1

  公开（公告）日：2001-09-18