(RS)-2,5-Dihydro-2-(1-hydroxy-1-methylethyl)-5,5-dimethyloxazol | 106011-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (RS)-2,5-Dihydro-2-(1-hydroxy-1-methylethyl)-5,5-dimethyloxazol
• 英文别名: 2-(5,5-dimethyl-2H-1,3-oxazol-2-yl)propan-2-ol
• CAS: 106011-26-1
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: GMDXAYPIYWGFTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-2,5-Dihydro-2-(1-hydroxy-1-methylethyl)-5,5-dimethyloxazol 在 camphor-10-sulfonic acid 、 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 (1'R,4R,4'R,4aS,7S,7'R,7aR,12bS)-3-(cyclopropylmethyl)-3',3',9',9'-tetramethylspiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,6'-2,5,8-trioxa-10-azatricyclo[5.2.1.04,10]decane]-4a,9-diol
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. 3: Synthesis of novel triplet drugs with the bis(epoxymethano) or bis(dimethylepoxymethano) structure (double-capped triplet)

  摘要：

  Novel double-capped triplet drugs, which have one pharmacophore unit and two epoxymethano or dimethylepoxymethano structures (termed cap or diMe-cap structures, respectively) were synthesized. Key intermediate oxazoline 16 derived from acetone enabled the effective synthesis of double-capped triplets. SYK-134 (7a) and SYK-135 (8a) with N-cyclopropylmethyl substituent and cap structures showed selectivities for the kappa opioid receptor. On the other hand, the N-Me series exhibited selectivities for the mu opioid receptor. The double-capped triplet drugs with diMe-cap structures preferred the mu receptor independently of their N-substituents. SYK-385 (19b), one of the mu-selective double-capped triplet drugs, showed the highest selectivity for the mu receptor among the reported mu-selective nonpeptide ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.023
• 作为产物：
  描述：

  2-羟基-2-甲基丙醛 在 sodium acetate 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成 (RS)-2,5-Dihydro-2-(1-hydroxy-1-methylethyl)-5,5-dimethyloxazol
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. 3: Synthesis of novel triplet drugs with the bis(epoxymethano) or bis(dimethylepoxymethano) structure (double-capped triplet)

  摘要：

  Novel double-capped triplet drugs, which have one pharmacophore unit and two epoxymethano or dimethylepoxymethano structures (termed cap or diMe-cap structures, respectively) were synthesized. Key intermediate oxazoline 16 derived from acetone enabled the effective synthesis of double-capped triplets. SYK-134 (7a) and SYK-135 (8a) with N-cyclopropylmethyl substituent and cap structures showed selectivities for the kappa opioid receptor. On the other hand, the N-Me series exhibited selectivities for the mu opioid receptor. The double-capped triplet drugs with diMe-cap structures preferred the mu receptor independently of their N-substituents. SYK-385 (19b), one of the mu-selective double-capped triplet drugs, showed the highest selectivity for the mu receptor among the reported mu-selective nonpeptide ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.023

文献信息

• 2(1-Hydroxy-1-methyl-ethyl)-5,5-dimethyl-delta 3-oxazolin und Verfahren zu seiner Herstellung
  申请人：HÜLS AKTIENGESELLSCHAFT

  公开号：EP0195954A2

  公开（公告）日：1986-10-01

  2(1-Hydroxy-1-methyl-ethyl)-5,5-dimethyl-Δ3-Oxazolin der Formel Zur Herstellung von 2(1-Hydroxy-1-methyl-ethyl)-5,5-dimethyl-Δ3-Oxazolin setzt man a-Hydroxyisobutyraldehyd mit Ammoniak oder wäßriger Ammoniaklösung bzw. dessen Acetal (Epoxid) mit wäßriger Ammoniaklösung bei Temperaturen von 20 bis 100°C um. Bevorzugt setzt man konzentrierte wäßrige Ammoniaklösung ein.

  式中的 2(1-羟基-1-甲基-乙基)-5,5-二甲基-Δ3-恶唑啉 为制备 2(1-羟基-1-甲基-乙基)-5,5-二甲基-Δ3-恶唑啉，a-羟基异丁醛与氨或氨水溶液或其缩醛（环氧化物）与氨水溶液在 20-100°C 的温度下反应。最好使用浓氨水溶液。
• Weber, Maya; Jakob, Juergen; Martens, Juergen, Liebigs Annalen der Chemie, 1992, # 1, p. 1 - 6
  作者：Weber, Maya、Jakob, Juergen、Martens, Juergen

  DOI：——

  日期：——
• BROCKHAUS, RUDOLF;FRANKE, HANS-JURGEN
  作者：BROCKHAUS, RUDOLF、FRANKE, HANS-JURGEN

  DOI：——

  日期：——
• ——
  作者：BROCKHAUS R.、 FRANKE H. -J.

  DOI：——

  日期：——
• Di-(tert.-butanol)-amin und Verfahren zu seiner Herstellung durch Hydrierung von 2(1-Hydroxy-1-methyl-ethyl)-5,5-dimethyl-1,3-Oxazolin
  申请人：HÜLS AKTIENGESELLSCHAFT

  公开号：EP0200917B1

  公开（公告）日：1988-08-03