(+/-)-erythro-3-(dimethylamino)-2-butanol | 55261-16-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-erythro-3-(dimethylamino)-2-butanol
• 英文别名: (2S,3R)-3-(dimethylamino)butan-2-ol
• CAS: 55261-16-0
• 化学式: C₆H₁₅NO
• 分子量: 117.191
• InChiKey: AINPAHMIZZLYDO-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-erythro-3-(dimethylamino)-2-butanol 以 乙醚 为溶剂， 反应 54.0h， 生成 (+)-erythro-5-methylmethadone
  参考文献：
  名称：

  Synthesis, x-ray crystallographic determination, and opioid activity of erythro-5-methylmethadone enantiomers. Evidence which suggests that .mu. and .delta. opioid receptors possess different stereochemical requirements

  摘要：

  Enantiomers of erythro-5-methylmethadone (3) were synthesized from optical antipodes of erythro-3-(dimethyl-amino)-2-butanol. X-ray crystallographic analysis of (-)-3 perchlorate revealed that it possesses the 5S,6S absolute configuration. It was found that (-)-3 is substantially more potent than its enantiomer (+)-3 as an opioid agonist in vivo and in vitro. In vitro tests (guinea pig ileal longitudinal muscle and mouse vas deferens preparations) suggest that (-)-3 mediates its effect chiefly through mu opioid receptors. On the other hand, (+)-3 and the more potent enantiomers of methadone, (-)-1, and isomethadone, (-)-2, appear to have less mu-receptor selectivity and interact with a greater fraction of delta receptors than does (-)-3. The fact that the solid-state conformation of (-)-3 differs from that of (-)-1 and (-)-2, which show great similarity in conformational features, suggests that mu and delta receptors have different conformational requirements. The possibility of different modes of interaction with a single opioid receptor population also is discussed.

  DOI：

  10.1021/jm00348a015
• 作为产物：
  描述：

  2,3-trans-epoxybutane 生成 (+/-)-erythro-3-(dimethylamino)-2-butanol
  参考文献：
  名称：

  Wilson; Lucas, Journal of the American Chemical Society, 1936, vol. 58, p. 2399

  摘要：

  DOI：

文献信息

• [EN] EGFR INHIBITORS<br/>[FR] INHIBITEURS D'EGFR
  申请人：BLUEPRINT MEDICINES CORP

  公开号：WO2022192431A1

  公开（公告）日：2022-09-15

  The present disclosure provides a compound represented by structural formula (1-0): or a pharmaceutically acceptable salt thereof useful for treating a cancer.

  本公开提供一种化合物，其结构式表示为（1-0）：或其药学上可接受的盐，用于治疗癌症。
• Conformational Aspects of Acetylcholine Receptor Sites. The Isomeric 3-Trimethylammonium-2-acetoxy-trans-decalin Halides¹ and the Isomeric α,β-Dimethylacetylcholine Halides²
  作者：Edward E. Smissman、Wendel L. Nelson、Jules B. LaPidus、James L. Day

  DOI：10.1021/jm00322a002

  日期：1966.7
• Rates of imine formation from acetone and some N,N-dimethyl vicinal diamines
  作者：Jack Hine、Yueting Chou

  DOI：10.1021/jo00317a001

  日期：1981.2
• WO2024059169A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis, x-ray crystallographic determination, and opioid activity of erythro-5-methylmethadone enantiomers. Evidence which suggests that .mu. and .delta. opioid receptors possess different stereochemical requirements
  作者：P. S. Portoghese、J. H. Poupaert、D. L. Larson、W. C. Groutas、G. D. Meitzner、D. C. Swenson、G. D. Smith、W. L. Duax

  DOI：10.1021/jm00348a015

  日期：1982.6

  Enantiomers of erythro-5-methylmethadone (3) were synthesized from optical antipodes of erythro-3-(dimethyl-amino)-2-butanol. X-ray crystallographic analysis of (-)-3 perchlorate revealed that it possesses the 5S,6S absolute configuration. It was found that (-)-3 is substantially more potent than its enantiomer (+)-3 as an opioid agonist in vivo and in vitro. In vitro tests (guinea pig ileal longitudinal muscle and mouse vas deferens preparations) suggest that (-)-3 mediates its effect chiefly through mu opioid receptors. On the other hand, (+)-3 and the more potent enantiomers of methadone, (-)-1, and isomethadone, (-)-2, appear to have less mu-receptor selectivity and interact with a greater fraction of delta receptors than does (-)-3. The fact that the solid-state conformation of (-)-3 differs from that of (-)-1 and (-)-2, which show great similarity in conformational features, suggests that mu and delta receptors have different conformational requirements. The possibility of different modes of interaction with a single opioid receptor population also is discussed.