8-bromo-6-chloro-2-(2-(1-tosyl-1H-indol-3-yl)ethyl)-chroman-4-one | 1138464-53-5

• 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-tosyl-1H-indol-3-yl)ethyl)-chroman-4-one
• 英文别名: 8-Bromo-6-chloro-2-[2-[1-(4-methylphenyl)sulfonylindol-3-yl]ethyl]-2,3-dihydrochromen-4-one
• CAS: 1138464-53-5
• 化学式: C₂₆H₂₁BrClNO₄S
• 分子量: 558.88
• InChiKey: DVBPDNRNGOAGSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloro-2-(2-(1-tosyl-1H-indol-3-yl)ethyl)-chroman-4-one 、 N-methylenebenzylamine 在 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以52%的产率得到1,3-dibenzyl-7-bromo-9-chloro-5-(2-(1-tosyl-1H-indol-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-chromeno[4,3-d]pyrimidine
  参考文献：
  名称：

  Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines

  摘要：

  Novel tricyclic N-benzylated chroman-4-one tetrahydropyrimidine derivatives have been prepared through a multi-component reaction between various 2-substituted chroman-4-one derivatives, N-methylenebenzylamine and a catalytic amount of proline under mild reaction conditions. The tricyclic structure of 1a was determined by NMR spectroscopy and confirmed by X-ray crystallography. An additional product, 2a, was isolated from the reaction mixture and its structure and conformation were determined by a combination of theoretical (Monte Carlo conformational search) and NMR-based (NOE and (3)J(HH) couplings) conformational analysis. The NMR analysis revealed one preferred geometry for 1a and 2a in CHCl3 solution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.077
• 作为产物：
  描述：

  3-(1-tosyl-1H-indol-3-yl)propanal 、 3'-溴-5'-氯-2'-羟基苯乙酮 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以88%的产率得到8-bromo-6-chloro-2-(2-(1-tosyl-1H-indol-3-yl)ethyl)-chroman-4-one
  参考文献：
  名称：

  Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines

  摘要：

  Novel tricyclic N-benzylated chroman-4-one tetrahydropyrimidine derivatives have been prepared through a multi-component reaction between various 2-substituted chroman-4-one derivatives, N-methylenebenzylamine and a catalytic amount of proline under mild reaction conditions. The tricyclic structure of 1a was determined by NMR spectroscopy and confirmed by X-ray crystallography. An additional product, 2a, was isolated from the reaction mixture and its structure and conformation were determined by a combination of theoretical (Monte Carlo conformational search) and NMR-based (NOE and (3)J(HH) couplings) conformational analysis. The NMR analysis revealed one preferred geometry for 1a and 2a in CHCl3 solution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.077

文献信息

• Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors
  作者：Maria Fridén-Saxin、Tina Seifert、Marie Rydén Landergren、Tiina Suuronen、Maija Lahtela-Kakkonen、Elina M. Jarho、Kristina Luthman

  DOI：10.1021/jm3005288

  日期：2012.8.23

  A series of substituted chromone/chroman-4-one derivatives has been synthesized and evaluated as novel inhibitors of SIRT2, an enzyme involved in aging-related diseases, e.g., neurodegenerative disorders. The analogues were efficiently synthesized in a one-step procedure including a base-mediated aldol condensation using microwave irradiation. The most potent compounds, with inhibitory concentrations in the low micromolar range, were substituted in the 2-, 6-, and 8-positions. Larger, electron-withdrawing substituents in the 6- and 8-positions were favorable. The most potent inhibitor of SIRT2 was 6,8-dibromo-2-pentylchroman-4-one with an IC50 of 1.5 mu M. The synthesized compounds show high selectivity toward SIRT2 over SIRT1 and SIRT3 and represent an important starting point for the development of novel SIRT2 inhibitors.
• 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.
• Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines
  作者：Maria Fridén-Saxin、Tina Seifert、Lars Kristian Hansen、Morten Grøtli、Mate Erdelyi、Kristina Luthman

  DOI：10.1016/j.tet.2012.06.077

  日期：2012.9

  Novel tricyclic N-benzylated chroman-4-one tetrahydropyrimidine derivatives have been prepared through a multi-component reaction between various 2-substituted chroman-4-one derivatives, N-methylenebenzylamine and a catalytic amount of proline under mild reaction conditions. The tricyclic structure of 1a was determined by NMR spectroscopy and confirmed by X-ray crystallography. An additional product, 2a, was isolated from the reaction mixture and its structure and conformation were determined by a combination of theoretical (Monte Carlo conformational search) and NMR-based (NOE and (3)J(HH) couplings) conformational analysis. The NMR analysis revealed one preferred geometry for 1a and 2a in CHCl3 solution. (C) 2012 Elsevier Ltd. All rights reserved.