N-benzyl-2-(3-hydroxyphenoxy)ethylamine | 129689-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-2-(3-hydroxyphenoxy)ethylamine
• 英文别名: 3-[2-(Benzylamino)ethoxy]phenol
• CAS: 129689-29-8
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: VBTFJGYCISLKEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄基(2-羟乙基)氨基甲酸叔丁酯 在 偶氮二甲酸二异丙酯 、 氢溴酸 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 N-benzyl-2-(3-hydroxyphenoxy)ethylamine
  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

• Selective .beta.3-adrenergic agonists of brown adipose tissue and thermogenesis. 2. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetamides
  作者：Ralph Howe、Balbir S. Rao、Brian R. Holloway、Donald Stribling

  DOI：10.1021/jm00088a010

  日期：1992.5

  The ester methyl [4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate (1) (R1 = OMe) had previously been identified as the most interesting member of a series of selective beta-3-adrenergic agonists of brown adipose tissue and thermogenesis in the rat. In vivo it acts mainly via the related acid 1 (R1 = OH). Amides have been examined to determine whether they have advantages over the ester. In particular, in the rat and dog the half-lives of amides of appropriate potency were no longer than those of the ester. The amide (S)-4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]-N-(2-methoxyethyl)phenoxyacetamide [S-27, ICI D7114] was selected as having properties consistent with a sustained-release formulation should that prove necessary. Unlike the ester it is resistant to hydrolysis in the gut lumen. Further testing of ICI D7114 has shown that in the rat, cat, and dog it stimulates the beta-3-adrenergic receptor in brown adipose tissue at doses lower than those at which it affects beta-1- and beta-2-adrenergic receptors in other tissues. Slimming effects were observed in the dog. ICI D7114 may be a selective thermogenic agent in man and may be useful in the treatment of obesity and diabetes.
• 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.