1-(2-甲基六氢-2-嘧啶基)乙酮 | 221073-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(2-甲基六氢-2-嘧啶基)乙酮
• 英文名称: 2-acetyl-2-methyl-hexahydropyrimidine
• 英文别名: Ethanone, 1-(hexahydro-2-methyl-2-pyrimidinyl)-；1-(2-methyl-1,3-diazinan-2-yl)ethanone
• CAS: 221073-75-2
• 化学式: C₇H₁₄N₂O
• 分子量: 142.201
• InChiKey: KXMGVZCBOKKOQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-甲基六氢-2-嘧啶基)乙酮 以 氯仿 为溶剂， 反应 168.0h， 以26%的产率得到6,7-dihydro-2,3-dimethyl-5H-1,4-diazepine
  参考文献：
  名称：

  一些1,4-二氮杂pine的合成和DNA链断裂活性。

  摘要：

  检查了1，3-丙二胺与α-二羰基化合物（1a-e）的反应，得到了各种稠合的杂环化合物，例如1，4-二氮杂（2）和3-嘧啶衍生物（3）。一些1,4-二氮杂（（2）具有DNA链断裂活性。

  DOI：

  10.1248/cpb.51.27
• 作为产物：
  描述：

  1,3-丙二胺 、 2,3-丁二酮 以 乙醚 为溶剂， 反应 0.5h， 以16%的产率得到1-(2-甲基六氢-2-嘧啶基)乙酮
  参考文献：
  名称：

  New compounds derived from dihydropyrazines having DNA strand-breakage activity

  摘要：

  Dihydropyrazine derivatives such as 2,3-dihydro-5,6-dimethylpyrazine (1), 2,3-dihydro-2,5,6-trimethylpyrazine (2) and 2,3-dihydro-2,2,5,6-teramethylpyrazine (3) were found to be transformed into (2R*, 3S*, 5R*)-1,2 ethylene-imino-1,7,10-triaza-2,3,6-trimethyl-3-hydroxy-spiro [4,5] decan-6-ene (4), the stereo-isomeric mixtures of 2,4aR*,7,9aS*-tetramethylcyclohexano [1,2-e: 4,5-e']-dipiperazin-6-ene (5) and (4aR*, 9aS*)-2,2,4a,7,7,9a-hexamethylcyclohexano [1,2-e: 4,5-e']-dipiperazin-6-ene (6), respectively. These dimerized compounds (4, 5 and 6), whose structures were determined by X-ray and nmr spectral analyses, showed almost the same DNA strand-breakage activity as their parent dihydropyrazines. The dimerization pathway is discussed on the basis of the PM3 calculation data. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01079-5

文献信息

• Reaction of 2,3-Butanedione with Propylenediamine Observed by 1H-Nmr Spectroscopy
  作者：Tadatoshi Yamaguchi、Shigeru Ito、Nobuko Mibu、Kunihiro Sumoto

  DOI：10.3987/com-01-9385

  日期：——

  2,3-Butanedione reacted with propylenediamine to form an initial intermediate: acetylated methyl-N-(3-aminopropyl) imine, which was a geometrical mixture of syn - and anti- isomers. The intermediate isomerized to anti- or syn-form via pyrimidine ring flip on heating. A steric factor of the isomers affected the formation of the final products. The mechanism based on NMR spectroscopy and molecular orbital calculation is proposed.

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