(1α,2α,4α,5α)-4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione) | 135683-26-0

• 英文名称: (1α,2α,4α,5α)-4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)
• 英文别名: 4-[(1R,2S,4R,5S)-2-(3,5-dioxopiperazin-1-yl)-4,5-dihydroxycyclohexyl]piperazine-2,6-dione
• CAS: 135683-26-0
• 化学式: C₁₄H₂₀N₄O₆
• 分子量: 340.336
• InChiKey: XCZYTNZZOSBWGB-FIRGSJFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3aα,5β,6β,7aα)-4,4'-(hexahydro-2,2-dimethyl-1,3-benzodioxole-5,6-diyl)bis(2,6-piperazinedione) 在 盐酸 作用下， 反应 0.05h， 以64%的产率得到(1α,2α,4α,5α)-4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)
  参考文献：
  名称：

  Syntheses and proton NMR conformational analyses of diastereomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)s and a synthetically related tricyclic octahydro-2,2-dimethyl-6-oxo-1,3-dioxolo[4,5-g]quinoxaline-5,8-diacetic acid ester

  摘要：

  Efficient syntheses for five of the six possible diastereoisomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis-(2,6-dioxopiperazine)s (5-9) and a synthetically related tricyclic 1,3-dioxolo[4,5-g]quinoxaline ring system 45 from their respective (4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate)s 11-16 via isopropylidene-protected intermediates are described. Solution conformations of all targets and several synthetic intermediates in DMSO-d6 were determined using H-1 NMR and NOE methods, and the structure for polyheterocycle 45, obtained during attempted preparation of the sixth possible dioxopiperazine diastereomer 10, was determined with the additional aid of 2D COSY, 2D HETCOR, and H-1-C-13 correlation of long-range coupling (COLOC). Taken together, these studies provide evidence for the differences in reaction conditions required for bis(dioxopiperazine) synthesis, a relatively comprehensive analysis of dioxopiperazine and hydroxyl substituent effects on cyclohexane DMSO-d6 solution conformations, and a preliminary analysis of aqueous solubility differences.

  DOI：

  10.1021/jo00018a039