8-bromo-6-chloro-2-(2-(1-naphthyl)ethyl)chroman-4-one | 1138464-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-bromo-6-chloro-2-(2-(1-naphthyl)ethyl)chroman-4-one
• 英文别名: 8-Bromo-6-chloro-2-(2-naphthalen-1-ylethyl)-2,3-dihydrochromen-4-one
• CAS: 1138464-49-9
• 化学式: C₂₁H₁₆BrClO₂
• 分子量: 415.714
• InChiKey: RGPZAHWLIUBWKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloro-2-(2-(1-naphthyl)ethyl)chroman-4-one 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 8-(3-aminopropyl)-6-chloro-2-(2-(1-naphthyl)ethyl)chroman-4-one
  参考文献：
  名称：

  Chroman-4-one and chromone based somatostatin β-turn mimetics

  摘要：

  A scaffold approach has been used to develop somatostatin beta-turn mimetics based on chroman-4-one and chromone ring systems. Such derivatives could adopt conformations resembling type II or type II' beta-turns. Side chain equivalents of the crucial Trp8 and Lys9 in somatostatin were introduced in the 2- and 8-positions of the scaffolds using efficient reactions. Interestingly, this proof-of-concept study shows that 4 and 9 have K-i-values in the low mu M range when evaluated for their affinity for the sst2 and sst4 receptors. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.02.046
• 作为产物：
  描述：

  3'-溴-5'-氯-2'-羟基苯乙酮 、 3-(naphthalen-1-yl)propanal 在 二异丙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以84%的产率得到8-bromo-6-chloro-2-(2-(1-naphthyl)ethyl)chroman-4-one
  参考文献：
  名称：

  Synthesis of 2-Alkyl-Substituted Chromone Derivatives Using Microwave Irradiation

  摘要：

  A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using diisopropylamine in EtOH at 170 degrees C for 1 h gave moderate to high yields (43-88%). The 4-chromanones could be further converted into highly functionalized 2,3,6,8-tetrasubstituted chromones in which a 3-substituent (acetate, amine, or bromine) was introduced via straightforward chemical transformations.

  DOI：

  10.1021/jo802783z

文献信息

• Synthesis of 2-Alkyl-Substituted Chromone Derivatives Using Microwave Irradiation
  作者：Maria Fridén-Saxin、Nils Pemberton、Krystle da Silva Andersson、Christine Dyrager、Annika Friberg、Morten Grøtli、Kristina Luthman

  DOI：10.1021/jo802783z

  日期：2009.4.3

  A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using diisopropylamine in EtOH at 170 degrees C for 1 h gave moderate to high yields (43-88%). The 4-chromanones could be further converted into highly functionalized 2,3,6,8-tetrasubstituted chromones in which a 3-substituent (acetate, amine, or bromine) was introduced via straightforward chemical transformations.
• Chroman-4-one and chromone based somatostatin β-turn mimetics
  作者：Maria Fridén-Saxin、Tina Seifert、Marcus Malo、Krystle da Silva Andersson、Nils Pemberton、Christine Dyrager、Annika Friberg、Kristian Dahlén、Erik A.A. Wallén、Morten Grøtli、Kristina Luthman

  DOI：10.1016/j.ejmech.2016.02.046

  日期：2016.5

  A scaffold approach has been used to develop somatostatin beta-turn mimetics based on chroman-4-one and chromone ring systems. Such derivatives could adopt conformations resembling type II or type II' beta-turns. Side chain equivalents of the crucial Trp8 and Lys9 in somatostatin were introduced in the 2- and 8-positions of the scaffolds using efficient reactions. Interestingly, this proof-of-concept study shows that 4 and 9 have K-i-values in the low mu M range when evaluated for their affinity for the sst2 and sst4 receptors. (C) 2016 Elsevier Masson SAS. All rights reserved.