3-methyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione | 373367-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-methyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione
• CAS: 373367-46-5
• 化学式: C₅H₅N₃O₂
• mdl: MFCD18805269
• 分子量: 139.114
• InChiKey: OVMICVINQYCFGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到6,7-dibromo-3-methyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione
  参考文献：
  名称：

  Are 1,2-Dihydrodiazetes Aromatic? An Experimental and Computational Investigation

  摘要：

  A thorough experimental and computational investigation of the aromaticity of the 1,2-dihydrodiazete ring system was carried out. The X-ray crystal structure of 1,2-dihydrodiazete 6 is reported, and the alkene-like reactivity of compound 6 is described. The compound's structure and reactivity suggest that 6 is not aromatic. This conclusion is corroborated by computational results on 6 and related compounds including homodesmotic reactions to test for aromatic stabilization, NICS calculations, and NBO calculations. Compound 6, and 1,2-dihydrodiazetes in general, are concluded to be strained heterocycles with no indication for aromatic stabilization.

  DOI：

  10.1021/jo026082m
• 作为产物：
  描述：

  3-Methyl-6-phenylsulfanyl-1,3,5-triaza-bicyclo[3.2.0]heptane-2,4-dione 在 间氯过氧苯甲酸 作用下， 以 氯苯 为溶剂， 反应 6.25h， 生成 3-methyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione
  参考文献：
  名称：

  通过Diels-Alder环加成法合成Delta（1）-1,2-二氮杂环丁烷。

  摘要：

  [反应：见正文]提出了一种合成Delta（1）-1,2-二氮杂tine的新方法。亲二烯体4与五个二烯的狄尔斯-阿尔德环加成反应以良好至优异的产率提供了环加合物。将获得的四个环加合物转化为相应的地西汀。

  DOI：

  10.1021/ol0164942

文献信息

• Thermal Decomposition of a Series of 1,2-Diazetines
  作者：Gary W. Breton、John H. Shugart

  DOI：10.1021/jo0351926

  日期：2003.10.1

  A homologous series of tricyclic diazetines (6a-c), differing by the number of methylene groups in the saturated bridges of the fused carbon bicycles, was synthesized. The DeltaH(not equal) of decomposition for each of the diazetines to afford N-2 and the corresponding alkene was determined experimentally: 6a, 31.7; 6b, 39.3; 6c, 38.8 kcal/mol. The ground-state strain energy of each diazetine was estimated utilizing computationally obtained DeltaH(f)'s for each of the experimentally investigated diazetines as well as several other diazetines whose DeltaHs(not equal,) had been previously reported in the literature. The sum of the ground-state strain energies and DeltaHs(not equal,) of decomposition for all of the diazetines was nearly constant, with an average value of 59 kcal/mol, suggesting that all of the diazetines decompose via the same mechanism. Generally, the higher the ground-state strain energy of the diazetine, the less the DeltaH(not equal) for decomposition. The decomposition transition states for 6a-c and 7 were modeled computationally at the RB3LYP/6-311+G(3df,2p)//UB3LYP/6-31+G(d,p) level. The agreement of the experimentally determined DeltaH(not equal) values with transition-state energies obtained computationally supports the reaction mechanism originally proposed by Yamabe that the elimination process occurs by an unsymmetrical, yet concerted, transition state with strong biradical character.
• Synthesis of Δ¹-1,2-Diazetines via a Diels−Alder Cycloaddition Approach
  作者：Gary W. Breton、John H. Shugart、Christine A. Hughey、Suzanne M. Perala、Alisa D. Hicks

  DOI：10.1021/ol0164942

  日期：2001.10.1

  [reaction: see text] A novel method for the synthesis of Delta(1)-1,2-diazetines is presented. Diels-Alder cycloaddition of dienophile 4 with five dienes afforded cycloadducts in good to excellent yields. Four of the obtained cycloadducts were converted to the corresponding diazetines.

  [反应：见正文]提出了一种合成Delta（1）-1,2-二氮杂tine的新方法。亲二烯体4与五个二烯的狄尔斯-阿尔德环加成反应以良好至优异的产率提供了环加合物。将获得的四个环加合物转化为相应的地西汀。
• Are 1,2-Dihydrodiazetes Aromatic? An Experimental and Computational Investigation
  作者：Gary W. Breton、Kenneth L. Martin

  DOI：10.1021/jo026082m

  日期：2002.9.1

  A thorough experimental and computational investigation of the aromaticity of the 1,2-dihydrodiazete ring system was carried out. The X-ray crystal structure of 1,2-dihydrodiazete 6 is reported, and the alkene-like reactivity of compound 6 is described. The compound's structure and reactivity suggest that 6 is not aromatic. This conclusion is corroborated by computational results on 6 and related compounds including homodesmotic reactions to test for aromatic stabilization, NICS calculations, and NBO calculations. Compound 6, and 1,2-dihydrodiazetes in general, are concluded to be strained heterocycles with no indication for aromatic stabilization.