(S)-8-叔丁基苯并二氢吡喃-4-胺 | 1228553-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: (S)-8-叔丁基苯并二氢吡喃-4-胺
• 英文名称: (S)-8-(tert-Butyl)chroman-4-amine
• 英文别名: (4S)-8-tert-butyl-3,4-dihydro-2H-chromen-4-amine
• CAS: 1228553-77-2
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: FNOIBLQXMSCOST-NSHDSACASA-N

物化性质

• 沸点：
  281.5±40.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-8-叔丁基苯并二氢吡喃-4-胺 在 水 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (S)-1-(8-tert-butylchroman-4-yl)-3-(1H-indazol-4-yl)urea
  参考文献：
  名称：

  Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists

  摘要：

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.056
• 作为产物：
  描述：

  2-叔丁基苯酚 在 吡啶 、 N-氯代丁二酰亚胺 、 palladium 10% on activated carbon 、 氨 、 氢气 、 silver(I) acetate 、 potassium carbonate 、 乙二醇 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 129.0h， 生成 (S)-8-叔丁基苯并二氢吡喃-4-胺
  参考文献：
  名称：

  Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists

  摘要：

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.056

文献信息

• Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists
  作者：Robert G. Schmidt、Erol K. Bayburt、Steven P. Latshaw、John R. Koenig、Jerome F. Daanen、Heath A. McDonald、Bruce R. Bianchi、Chengmin Zhong、Shailen Joshi、Prisca Honore、Kennan C. Marsh、Chih-Hung Lee、Connie R. Faltynek、Arthur Gomtsyan

  DOI：10.1016/j.bmcl.2011.01.056

  日期：2011.3

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.