1,3-dimethylcyclooctapyrimidine-2,4-dione | 134886-54-7

• 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: 1,3-dimethylcyclooctapyrimidine-2,4-dione
• CAS: 134886-54-7
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: QHBPSYZFANELEC-PBHGPXFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-dimethylcyclooctapyrimidine-2,4-dione 、 三氟乙酸 以 环己烷 为溶剂， 反应 3.0h， 以28%的产率得到9H-6,6a-dihydro-1,3-dimethyl-2,4-dioxopentaleno[6a,1-d]pyrimidin-6-yl trifluoroacetate
  参考文献：
  名称：

  Photoinduced Transannular Reaction of 1,3-Dimethyl-Cyclooctapyrimidine-2,4-Diones¶

  摘要：

  This article reports further elaboration of the authors' investigations on the acid-catalyzed photorearrangements undergone by derivatives of 1,3-dimethylcyclooctapyrimidine-2,4-dione. In this case the results are represented for compounds containing a simple methyl or fluorine substituent at different positions in the eight-membered ring. Upon photolysis in frozen benzene containing trifluoroacetic acid, the monomethylated compounds give varying yields of pentalenopyrimidinedione products that are not generated from the fluorinated compounds, which are either inert or undergo hydration accompanied by dehyrofluorination. Plausible mechanisms are advanced to account for the formation of the observed photoproduct species. The work represents an interesting extension and uncovered new aspects of the photorearrangement process.

  DOI：

  10.1562/0031-8655(2002)075<0579:ptrodc>2.0.co;2
• 作为产物：
  描述：

  6-氯-1,3-二甲基脲嘧啶 、 苯 在 三氟乙酸 作用下， 反应 10.0h， 以62%的产率得到1,3-dimethylcyclooctapyrimidine-2,4-dione
  参考文献：
  名称：

  Acid-catalyzed Photoreaction of 6-Chloro-1,3-dimethyluracil in Benzene; Synthesis of Cyclooctapyrimidine-2,4-dione

  摘要：

  The photolysis of 6-chloro-1,3-dimethyluracil in benzene afforded 1,3-dimethyl-6-phenyluracil, while the photoreaction in the presence of trifluoroacetic acid afforded 1,3-dimethylcyclooctapyrimidine-2.4-dione as a major product.

  DOI：

  10.3987/com-90-5655

文献信息

• Synthesis of Cyclooctapyrimidine-2,4-diones by Photocycloadition of 6-Chloro-1,3-dimethyluracil to Benzenes in the Presence of Trifluoroacetic Acid.
  作者：Kazue OHKURA、Nobuhiko KANAZASHI、Koh-ichi SEKI

  DOI：10.1248/cpb.41.239

  日期：——

  Photoreaction of 6-chloro-1, 3-dimethyluracil in benzene and monosubstituted benzenes furnished cycloaddition products, cyclooctapyrimidine-2, 4-dione derivatives, in the presence of trifluoroacetic acid.

  在三氟乙酸存在下，6-氯-1, 3-二甲基尿嘧啶在苯和单取代苯中的光反应产生了环加成产物，即环辛基嘧啶-2, 4-二酮衍生物。
• Acid-Catalyzed Photoreaction of 6-Chloro-1,3-dimethyluracil in Frozen Benzene: Formation of Novel Cycloadducts, Tetrahydropentaleno[1,2-e]pyrimidine-2,4-dione Derivatives
  作者：Kazue Ohkura、Yukari Noguchi、Koh-ichi Seki

  DOI：10.1246/cl.1997.99

  日期：1997.1

  Contrasting to the photoreaction of 6-chloro-1,3-dimethyluracil in benzene at ambient temperature in the presence of trifluoroacetic acid, whereby 1,3-dimethylcyclooctapyrimidine was produced as a sole cycloadduct, the similar photoreaction in frozen benzene at −15 ∼ −20 °C proceeded quite differently to give three novel photocycloadducts, 7-chloro-1,3-dimethyl-4b,5,7a,8-tetrahydropentaleno[1,2-e]pyrimidine-2

  与 6-氯-1,3-二甲基尿嘧啶在室温下在三氟乙酸存在下在苯中的光反应相反，1,3-二甲基环八嘧啶作为唯一的环加合物产生，在-15 ∼ - 在冷冻苯中的类似光反应20 °C 进行完全不同，得到三种新型光环加合物，7-氯-1,3-二甲基-4b,5,7a,8-四氢戊烯[1,2-e]嘧啶-2,4-二酮，5-氯- 1,3-二甲基-4b,7,7a,8-四氢戊烯[1,2-e]嘧啶-2,4-二酮和6-氯-10,12-二氮杂五环[6.4.0.01,3.02,5.04,8 ]十二烷-9,11-二酮。
• Acid-catalyzed Photoreaction of 6-Chloro-1,3-dimethyluracil in Frozen Benzene: Formation of Photocycloadducts and Their Isomerization through Photo-Diels-Alder Reaction
  作者：Koh-ichi Seki、Kazue Ohkura、Yukari Noguchi

  DOI：10.3987/com-97-s(n)66

  日期：——
• Ohkura; Noguchi; Seki, Heterocycles, 1998, vol. 49, # 1, p. 59 - 62
  作者：Ohkura、Noguchi、Seki

  DOI：——

  日期：——
• Ohkura, Kazue; Noguchi, Yukari; Seki, Koh-Ichi, Heterocycles, 1997, vol. 46, # 1, p. 141 - 144
  作者：Ohkura, Kazue、Noguchi, Yukari、Seki, Koh-Ichi

  DOI：——

  日期：——