6,7-bis(1-methyl-1H-indol-3-yl)-2H-thiazolo[3,2-a]pyrimidin-5(3H)-one | 1262058-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6,7-bis(1-methyl-1H-indol-3-yl)-2H-thiazolo[3,2-a]pyrimidin-5(3H)-one
• 英文别名: 6,7-Bis(1-methylindol-3-yl)-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one；6,7-bis(1-methylindol-3-yl)-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one
• CAS: 1262058-60-5
• 化学式: C₂₄H₂₀N₄OS
• 分子量: 412.515
• InChiKey: HEWKCPKKFDRNDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,6-bis(1-methyl-1H-indol-3-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 、 1,2-二溴乙烷 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以66%的产率得到6,7-bis(1-methyl-1H-indol-3-yl)-2H-thiazolo[3,2-a]pyrimidin-5(3H)-one
  参考文献：
  名称：

  Design and synthesis of novel 5,6-bisindolylpyrimidin-4-ones structurally related to ruboxistaurin (LY333531)

  摘要：

  2,3-Bis(1-methyl-1H-indol-3-yl) methyl-3-oxopropionate is a key intermediate in the synthesis of a new family of LY333531 analogues. Base-mediated cyclocondensation with thiourea afforded novel 5,6-bis(1-methyl-1H-indol-3-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one, which was efficiently converted to the pyrimidin-2,4(1H,3H)-dione congener. Synthesis of a six-membered K-252c analogue, 5,6-bis(1-methyl-1H-indol-3-yl)pyrimidin-4(3H)-one, is also described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.020

文献信息

• Design and synthesis of novel 5,6-bisindolylpyrimidin-4-ones structurally related to ruboxistaurin (LY333531)
  作者：Larry T. Pierce、Michael M. Cahill、Florence O. McCarthy

  DOI：10.1016/j.tet.2010.10.020

  日期：2010.12

  2,3-Bis(1-methyl-1H-indol-3-yl) methyl-3-oxopropionate is a key intermediate in the synthesis of a new family of LY333531 analogues. Base-mediated cyclocondensation with thiourea afforded novel 5,6-bis(1-methyl-1H-indol-3-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one, which was efficiently converted to the pyrimidin-2,4(1H,3H)-dione congener. Synthesis of a six-membered K-252c analogue, 5,6-bis(1-methyl-1H-indol-3-yl)pyrimidin-4(3H)-one, is also described. (C) 2010 Elsevier Ltd. All rights reserved.