3-methyl-2,3-dihydro-2-thioxo-pyrimidin-4(1H)-one | 576-28-3

• 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: 3-methyl-2,3-dihydro-2-thioxo-pyrimidin-4(1H)-one
• 英文别名: 3-methyl-2,3-dihydro-2-thioxo-4(1H)-pyrimidinone；3-methyl-2-thiouracil；3-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one；3-Methyl-2-thio-uracil；3-methyl-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 576-28-3
• 化学式: C₅H₆N₂OS
• mdl: MFCD00969987
• 分子量: 142.181
• InChiKey: KMJMDWDBNHZINA-UHFFFAOYSA-N

物化性质

• 熔点：
  292-294 °C(Solv: ethanol (64-17-5))
• 沸点：
  216.4±23.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-methyl-2,3-dihydro-2-thioxo-pyrimidin-4(1H)-one 、 臭氧 以25%的产率得到
  参考文献：
  名称：

  MATSUI, MASAKI;KAMIYA, KAZUSAKI;KAWAMURA, SHIGEO, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2939-2941

  摘要：

  DOI：
• 作为产物：
  描述：

  3-methyl-2-thioxo-2,3,r-4a,c-5,c-8,c-8a-hexahydro-5,8-methanoquinazolin-4(1H)-one 反应 0.17h， 生成 3-methyl-2,3-dihydro-2-thioxo-pyrimidin-4(1H)-one
  参考文献：
  名称：

  Stajer, Geza; Szabo, Angela E.; Pintye, Janos, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2483 - 2488

  摘要：

  DOI：

文献信息

• Ozonization of Thio- and Azauracils
  作者：Masaki Matsui、Kazusaki Kamiya、Shigeo Kawamura、Katsuyoshi Shibata、Hiroshige Muramatsu

  DOI：10.1246/bcsj.62.2939

  日期：1989.9

  The reactions of 2-thiouracils and azauracils with ozone have been examined. 2-Thiouracils were ozonized to give the corresponding 4(3H)-pyrimidinones and uracils. Ozone attacks the thiocarbonyl moiety and the desulfurization process to give 4(3H)-pyrimidinones competes with the oxidation process to give uracils. 5-Azauracil was stable for ozone, while 6-azauracil readily reacted with ozone to give parabanic acid.

  对2-硫尿嘧啶和氮杂尿嘧啶与臭氧的反应进行了研究。2-硫尿嘧啶经臭氧化反应生成相应的4(3H)-嘧啶酮和尿嘧啶。臭氧攻击硫碳基团，去硫过程生成4(3H)-嘧啶酮与氧化过程生成尿嘧啶之间存在竞争。5-氮杂尿嘧啶对臭氧稳定，而6-氮杂尿嘧啶则容易与臭氧反应生成巴拉班酸。
• Bernath, G., Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 9-10, p. 509 - 530
  作者：Bernath, G.

  DOI：——

  日期：——
• Friot, Celine; Reliquet, Alain; Reliquet, Francoise, Synthesis, 2000, # 5, p. 695 - 702
  作者：Friot, Celine、Reliquet, Alain、Reliquet, Francoise、Meslin, Jean Claude

  DOI：——

  日期：——
• Synthesis and Structure of Norbornane/ene-fused Thiouracils and Thiazino[3,2-a]pyrimidinones
  作者：Géza Stájer、Angela E. Szabó、Pál Sohár

  DOI：10.3987/com-99-8560

  日期：——

  Ethyl diexo-3-aminobicyclo [2.2.1]heptane- and -hept-5-ene-2-carboxylates (la,b) and the diendo derivatives were transformed with thiophosgene to the isothiocyanates (2a,b and 3a,b) and then cyclized to the norbornane/enecondensed 2-thioxopyrimidin-4-ones (4a,b and 5a,b). On heating, the norbornene compounds (4b and 5b) furnished thiouracil (6) via cyclopentadiene elimination. With dimethyl acetylenedicarboxylate, the thioxopyrimidinones (4a,b) and (5a,b) form angularly-fused [1,3]thiazino[3,2-a]pyrimidinones (7a,b and 8a,b). On heating, 7b decomposes to give 3-methyl-2,3-dihydro-2-thioxo-4(1H)-pyrimidinone (9) in a retro Diels-Alder process by methyl migration and splitting-off of cyclopentadiene. The structures were elucidated by IR and NMR spectroscopies, with DNOE, DEFT and 2D-HSC techniques.
• STAJER, G.;SZABO, A. E.;PINTYE, J.;BERNATH, G.;SOHAR, P., J. CHEM. SOC. PERKIN TRANS., 1985, 1, N 11, 2483-2487
  作者：STAJER, G.、SZABO, A. E.、PINTYE, J.、BERNATH, G.、SOHAR, P.

  DOI：——

  日期：——

表征谱图