2-(5-fluoro-2-methoxy-phenoxy)ethylchloride | 125960-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-fluoro-2-methoxy-phenoxy)ethylchloride
• 英文别名: 2-(5-fluoro-2-methoxyphenoxy)ethyl chloride；2-(2-chloroethoxy)-4-fluoroanisole；2-(2-chloroethoxy)-4-fluoro-1-methoxybenzene
• CAS: 125960-66-9
• 化学式: C₉H₁₀ClFO₂
• 分子量: 204.629
• InChiKey: DPIYABQLUSFISJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-fluoro-2-methoxy-phenoxy)ethylchloride 在 sodium azide 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 [2-(5-Fluoro-1H-indol-3-yl)ethyl]-[2-(5-fluoro-2-methoxy-phenoxy)-ethyl]-amine
  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-甲氧基苯酚 、 1-溴-2-氯乙烷 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以76%的产率得到2-(5-fluoro-2-methoxy-phenoxy)ethylchloride
  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-aryloxyethyl-indoly-alkylamines for the treatment of depression
  申请人：American Home Products Corp.

  公开号：US06121307A1

  公开（公告）日：2000-09-19

  Compounds useful for alleviating symptoms of depression are provided which have the following formula: wherein: R.sub.1 is hydrogen, lower alkyl or aryl; R.sub.2 is hydrogen, lower alkyl, phenyl or substituted phenyl; X and Y are each, independently, hydrogen, lower alkyl, lower alkoxy, or halogen, or together combine with the carbon atoms to which they are attached to complete a pyranyl, dihydrofuranyl, furanyl, or dioxanyl, group; Z is hydrogen, halogen or lower alkoxy; with the proviso that when X, Y or Z represent lower alkoxy, they are not present at the ortho position; W is hydrogen, halogen, lower alkyl, cyano or a trifluoromethyl group; and n is 2-5; or pharmaceutically acceptable salts thereof.

  提供了用于缓解抑郁症症状的化合物，其具有以下结构式：其中：R.sub.1为氢、低碳基或芳基；R.sub.2为氢、低碳基、苯基或取代苯基；X和Y分别独立地为氢、低碳基、低烷氧基或卤素，或者与它们连接的碳原子结合在一起形成吡喃基、二氢呋喃基、呋喃基或二氧杂环基；Z为氢、卤素或低烷氧基；但当X、Y或Z代表低烷氧基时，它们不位于邻位；W为氢、卤素、低碳基、氰基或三氟甲基基团；n为2-5；或其药用盐。
• Phenoxyethylamine derivatives, for preparing the same and composition
  申请人：Hokuriku Pharmaceutical Co., Ltd.

  公开号：US04971990A1

  公开（公告）日：1990-11-20

  Phenoxyethylamine derivatives represented by the general formula (I): ##STR1## wherein R.sub.1 and R.sub.5 represent lower-alkyl, R.sub.2 and R.sub.3, which may be the same or different, each represents hydrogen or lower-alkyl, or ##STR2## represents a 5- or 6-membered ring system which may include nitrogen, oxygen or sulfur as a ring membered atom, R.sub.4 represents hydrogen or lower-alkyl, and n represents an integer selected from 1 to 3, their optical isomers and pharmacologically-acceptable acid addition salts, which exhibit excellent .alpha..sub.1 -blocking activity, a process for their preparation, pharmaceutical compositions thereof, and a method for the treatment of a subject afflicted with hypertension or dysuria by administrating such a compound, are all disclosed.

  本发明揭示了一种由通式（I）表示的苯氧乙胺衍生物：##STR1## 其中R.sub.1和R.sub.5表示较低的烷基，R.sub.2和R.sub.3，可以相同或不同，每个表示氢或较低的烷基，或##STR2##表示一个5-或6-成员环系，其中可以包括氮、氧或硫作为环成员原子，R.sub.4表示氢或较低的烷基，n表示选择从1到3的整数，其光学异构体和药理学上可接受的酸加盐，表现出优异的α.sub.1-阻断活性，其制备方法，制药组合物以及通过管理此类化合物治疗患有高血压或排尿困难的受试者的方法。
• Phenoxyethylamine derivatives, process for preparing the same, and composition for exhibiting excellent alpha-1-blocking activity containing the same
  申请人：Hokuriku Pharmaceutical Co.,Ltd

  公开号：EP0331943A1

  公开（公告）日：1989-09-13

  Phenoxyethylamine derivatives represented by the general formula (I): wherein R₁ and R₅ represent lower-alkyl, R₂ and R₃, which may be the same or different, each represents hydrogen or lower-alkyl, or represents a 5- or 6-membered ring system which may include nitrogen, oxygen or sulfur as a ring membered atom, R₄ represents hydrogen or lower-alkyl, and n represents an integer selected from 1 to 3, their optical isomers and pharmacologically-acceptable acid addition salts, which exhibit excellent α₁-blocking activity, a process for their preparation, pharmaceutical compositions thereof, and a method for the treatment of a subject afflicted with hypertension or dysuria by administrating such a compound, are all disclosed.

  通式(I)代表的苯氧基乙胺衍生物： 其中 R₁ 和 R₅ 代表低级烷基，R₂ 和 R₃ 可以相同或不同，各自代表氢或低级烷基，或 代表可包括氮、氧或硫作为环成员原子的 5 或 6 元环系统，R₄ 代表氢或低级烷基，n 代表选自 1 至 3 的整数，它们的光学异构体和药理学上可接受的酸加成盐、本发明公开了具有优异α₁阻断活性的光学异构体和药理学上可接受的酸加成盐、其制备工艺、药物组合物，以及通过施用这种化合物治疗高血压或排尿困难患者的方法。
• 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