1-(4-Bromo-1,3-thiazol-2-yl)-3-methylbutan-1-one | 1245503-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Bromo-1,3-thiazol-2-yl)-3-methylbutan-1-one
• 英文别名: 1-(4-bromo-1,3-thiazol-2-yl)-3-methylbutan-1-one
• CAS: 1245503-22-3
• 化学式: C₈H₁₀BrNOS
• 分子量: 248.143
• InChiKey: RMWMUJAOCPEQIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-Bromo-1,3-thiazol-2-yl)-3-methylbutan-1-one 在 CBS 作用下， 生成 (S)-1-(4-bromothiazol-2-yl)-3-methylbutan-1-ol
  参考文献：
  名称：

  Synthesis and activity of the archazolid western hemisphere

  摘要：

  一种收敛且可扩展的archazolid西半球合成已经完成。随后，利用基于拟南芥的便捷V-ATPase检测法，对该化合物与先前制备的东半球结构域的V-ATPase抑制活性进行了测试。

  DOI：

  10.1039/c1ob06446k
• 作为产物：
  描述：

  2,4-二溴噻唑 、 N-methoxy-N,3-dimethylbutanamide 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以88%的产率得到1-(4-Bromo-1,3-thiazol-2-yl)-3-methylbutan-1-one
  参考文献：
  名称：

  Synthesis and evaluation of an Iejimalide-archazolid chimera

  摘要：

  Even though the macrolides of the iejimalide family are of marine origin, whereas those of the archazolid series derive from terrestrial myxobacteria, a comparison of their constitution, stereochemistry, and biological activity suggests that these natural products are close structural and functional relatives. Guided by this perception, compound 5 was prepared, which hybridizes the macrolactone core of iejimalide B (2) with the tail of archazolid A (3). The cytotoxicity profile of this chimera, as determined with a panel of 12 human cancer cell lines, corresponds to that of the parent compound 2, although its potency is lower. This outcome may be interpreted on the basis of molecular dynamics calculations, which suggest that the low energy conformations of 2 and 5 are similar but the energetic barriers between the relevant conformers are distinctly higher for the hybrid structure. The synthesis of 5 hinged on a regioselective functionalization of 2,4-dibromothiazole 6, a highly selective CBS-reduction of ketone 8, a Suzuki cross coupling of vinyl boronate 17 with the elaborate alkenyl iodide 16, and a productive closure of the macrocycle by RCM, which requires the selective activation of two out of eight double bonds present in the cyclization precursor 20 by the second-generation Grubbs catalyst 21. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.043

文献信息

• Synthesis and activity of the archazolid western hemisphere
  作者：Ann B. Tran、Geoffrey C. Melly、Ryan Doucette、Brook Ashcraft、Leanne J. Sebren、Nathan Havko、Jeffery C. Young、Gregory W. O'Neil

  DOI：10.1039/c1ob06446k

  日期：——

  A convergent and scalable synthesis of the archazolid western hemisphere has been completed. The V-ATPase inhibitory activity of this compound along with a previously prepared eastern domain was then tested using a convenient Arabidopsis-based V-ATPase assay.

  一种收敛且可扩展的archazolid西半球合成已经完成。随后，利用基于拟南芥的便捷V-ATPase检测法，对该化合物与先前制备的东半球结构域的V-ATPase抑制活性进行了测试。
• Synthesis and evaluation of an Iejimalide-archazolid chimera
  作者：Emilie Moulin、Cristina Nevado、Julien Gagnepain、Gerhard Kelter、Heinz-Herbert Fiebig、Alois Fürstner

  DOI：10.1016/j.tet.2010.05.043

  日期：2010.8

  Even though the macrolides of the iejimalide family are of marine origin, whereas those of the archazolid series derive from terrestrial myxobacteria, a comparison of their constitution, stereochemistry, and biological activity suggests that these natural products are close structural and functional relatives. Guided by this perception, compound 5 was prepared, which hybridizes the macrolactone core of iejimalide B (2) with the tail of archazolid A (3). The cytotoxicity profile of this chimera, as determined with a panel of 12 human cancer cell lines, corresponds to that of the parent compound 2, although its potency is lower. This outcome may be interpreted on the basis of molecular dynamics calculations, which suggest that the low energy conformations of 2 and 5 are similar but the energetic barriers between the relevant conformers are distinctly higher for the hybrid structure. The synthesis of 5 hinged on a regioselective functionalization of 2,4-dibromothiazole 6, a highly selective CBS-reduction of ketone 8, a Suzuki cross coupling of vinyl boronate 17 with the elaborate alkenyl iodide 16, and a productive closure of the macrocycle by RCM, which requires the selective activation of two out of eight double bonds present in the cyclization precursor 20 by the second-generation Grubbs catalyst 21. (C) 2010 Elsevier Ltd. All rights reserved.