N-phenethyl-4-phenylbutan-1-amine | 136534-64-0

• 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-phenethyl-4-phenylbutan-1-amine
• 英文别名: phenethyl-(4-phenyl-butyl)-amine；4-Phenaethylamino-1-phenyl-butan；Phenaethyl-(4-phenyl-butyl)-amin；N-(4-phenylbutyl)phenethylamine；4-phenyl-N-(2-phenylethyl)butan-1-amine
• CAS: 136534-64-0
• 化学式: C₁₈H₂₃N
• 分子量: 253.387
• InChiKey: HMGFNEMDDFFJES-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  388.9±21.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-苯基丁酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 N-phenethyl-4-phenylbutan-1-amine
  参考文献：
  名称：

  Structure−Activity Relationships for a Series of Bis(phenylalkyl)amines:  Potent Subtype-Selective Inhibitors of N-Methyl-d-aspartate Receptors

  摘要：

  A series of bis(phenylalkyl)amines, structural analogues of ifenprodil and nylidrin, were synthesized and tested for antagonism of N-methyl-D-aspartate (NMDA) receptors. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The bis(phenylalkyl)amines were selective antagonists of NR1A/2B receptors. Assayed under steady-state conditions, the most potent of these, N-[2-(4-hydroxyphenyl)ethyl]-5-phenylpentylamine hydrochloride (20), has an IC50 value of 8 nM and > 1000-fold selectivity with respect to NR1A/2A and NR1A/2C receptors. The structure-activity relationship of the bis(phenylalkyl)amine series indicates that the piperidine ring and alkyl chain substitutions common to NR2B-selective antagonists such as ifenprodil, CP 101,606, and Ro 25-6981 are not necessary to generate potent and selective ligands. The primary determinants of potency are the phenolic OH group, acting as a hydrogen bond donor, the distance between the two rings, and an electrostatic interaction between the receptor and the basic nitrogen atom. This study provides a framework for designing structurally novel NR2B-selective antagonists which may be useful for treatment of a variety of neurological disorders.

  DOI：

  10.1021/jm980235+

文献信息

• Two‐Step Protocol for Iodotrimethylsilane‐Mediated Deoxy‐Functionalization of Alcohols
  作者：Yuming Chen、Ru He、Hongjian Song、Guoqing Yu、Chenglin Li、Yuxiu Liu、Qingmin Wang

  DOI：10.1002/ejoc.202001602

  日期：2021.2.19

  protocol for iodotrimethylsilane‐mediated deoxy‐functionalization of primary and secondary alcohols was described. This protocol involves iodination of alcohol and then replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non‐acidic pre‐nucleophiles can be used in this protocol and configuration of alcohols can be retained.

  描述了碘代三甲基硅烷介导的伯醇和仲醇的脱氧官能化的两步协议。该协议涉及酒精的碘化，然后被N，S或O亲核试剂取代。与传统的Mitsunobu反应相比，该方案可以使用非酸性的亲核试剂，并且可以保留醇的配置。
• 将醇进行脱氧官能化和脱氧活化的方法与醇官能化物质
  申请人：山东博苑医药化学股份有限公司

  公开号：CN114716345A

  公开（公告）日：2022-07-08

  本发明涉及有机合成领域，公开了一种将醇进行脱氧官能化和脱氧活化的方法与醇官能化物质，该方法包括：(1)在第一溶剂中，在活化剂存在下，将醇进行脱氧活化，得到碘代物中间体；(2)在第二溶剂中，在亲核试剂存在下，将所述碘代物中间体进行官能化。本发明提供的方法操作简便、易于分离纯化。
• Kuelz et al., Chemische Berichte, 1939, vol. 72, p. 2161,2166
  作者：Kuelz et al.

  DOI：——

  日期：——
• SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：EP0591426A1

  公开（公告）日：1994-04-13
• US6057371A
  申请人：——

  公开号：US6057371A

  公开（公告）日：2000-05-02