N-[2-(2-methoxyphenoxy)ethyl]-N-benzylcarbamic acid tert-butyl ester | 204122-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[2-(2-methoxyphenoxy)ethyl]-N-benzylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-benzyl-N-[2-(2-methoxyphenoxy)ethyl]carbamate
• CAS: 204122-21-4
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: AVFKEOKTYAOEAT-UHFFFAOYSA-N

物化性质

• 沸点：
  472.9±38.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(2-methoxyphenoxy)ethyl]-N-benzylcarbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以96%的产率得到N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐
  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：

  N-苄基乙醇胺 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 N-[2-(2-methoxyphenoxy)ethyl]-N-benzylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  New generation dopaminergic agents. 2. Discovery of 3-OH-phenoxyethylamine and 3-OH-N1-phenylpiperazine dopaminergic templates

  摘要：

  Described in this report is a systematic study which led to the identification of two new dopamine D-2 partial agonists (5 and 17). Phenols 5 and 17 represent prototypes of two new classes of D-2 partial agonists as well as templates for the future design of novel dopaminergic agents. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00014-6

文献信息

• Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of <i>N</i>-Aryloxyethylindolylalkylamines
  作者：Richard E. Mewshaw、Dahui Zhou、Ping Zhou、Xiaojie Shi、Geoffrey Hornby、Taylor Spangler、Rosemary Scerni、Deborah Smith、Lee E. Schechter、Terrance H. Andree

  DOI：10.1021/jm0304010

  日期：2004.7.1

  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.
• New generation dopaminergic agents. 2. Discovery of 3-OH-phenoxyethylamine and 3-OH-N1-phenylpiperazine dopaminergic templates
  作者：Richard E. Mewshaw、Morris Husbands、Elizabeth S. Gildersleeve、Michael B. Webb、Xiaojie Shi、Hossein Mazandarani、Mark I. Cockett、Rafal Ochalski、Julie A. Brennan、Magid Abou-Gharbia、Karen Marquis、Georgia B. McGaughey、Joseph Coupet、Terrance H. Andree

  DOI：10.1016/s0960-894x(98)00014-6

  日期：1998.2

  Described in this report is a systematic study which led to the identification of two new dopamine D-2 partial agonists (5 and 17). Phenols 5 and 17 represent prototypes of two new classes of D-2 partial agonists as well as templates for the future design of novel dopaminergic agents. (C) 1998 Elsevier Science Ltd. All rights reserved.