5-(1-adamantyl)-dihydro-2-thioxopyrimidine-4,6(1H,5H)-dione | 34070-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(1-adamantyl)-dihydro-2-thioxopyrimidine-4,6(1H,5H)-dione
• 英文别名: 5-(1-adamantyl)-2-thiobarbituric acid；5-adamantan-1-yl-2-thioxo-dihydro-pyrimidine-4,6-dione；5-(1-Adamantyl)-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 34070-91-2
• 化学式: C₁₄H₁₈N₂O₂S
• 分子量: 278.375
• InChiKey: SSKUKZUIPXXXSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 1-金刚烷醇 在 三氟乙酸 作用下， 反应 3.0h， 以59%的产率得到5-(1-adamantyl)-dihydro-2-thioxopyrimidine-4,6(1H,5H)-dione
  参考文献：
  名称：

  Studies on the Adamantylation ofN-Heterocycles and Nucleosides

  摘要：

  Adamantylation of several N-heterocycles and of two ribonucleosides (uridine and toyocamycin) was studied. The exact substitution position by the adamantyl carbocation generated tram adamantan-1-ol in CF3COOH depends on the nature of the heterocyclic substrate. Thus, adamantylation of an additional exocyclic amino group (see Scheme 1), N-adamantylation of the heterocycle (Scheme 2), C-adamantylation of the heterocycle (Scheme 3), as well as the formation of heterocyclic N-adamantylcarboxamides via the Ritter reaction (Scheme 4) are possible. The structures of the reaction products were determined by means of elemental analysis and NMR, UV,and IR spectroscopy.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<2020::aid-hlca2020>3.0.co;2-p

文献信息

• Studies on the Adamantylation ofN-Heterocycles and Nucleosides
  作者：Zygmunt Kazimierczuk、Andrzej Orzeszko

  DOI：10.1002/(sici)1522-2675(19991110)82:11<2020::aid-hlca2020>3.0.co;2-p

  日期：1999.11.10

  Adamantylation of several N-heterocycles and of two ribonucleosides (uridine and toyocamycin) was studied. The exact substitution position by the adamantyl carbocation generated tram adamantan-1-ol in CF3COOH depends on the nature of the heterocyclic substrate. Thus, adamantylation of an additional exocyclic amino group (see Scheme 1), N-adamantylation of the heterocycle (Scheme 2), C-adamantylation of the heterocycle (Scheme 3), as well as the formation of heterocyclic N-adamantylcarboxamides via the Ritter reaction (Scheme 4) are possible. The structures of the reaction products were determined by means of elemental analysis and NMR, UV,and IR spectroscopy.