4-亚甲基-1,2-二氮杂环戊烯 | 10496-76-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-亚甲基-1,2-二氮杂环戊烯
• 英文名称: 4-methylene-1-pyrazoline
• 英文别名: 4-Methylen-1-pyrazolin；4-methylidene-3,5-dihydropyrazole
• CAS: 10496-76-1
• 化学式: C₄H₆N₂
• 分子量: 82.105
• InChiKey: HEPNIHPVRLJVFS-UHFFFAOYSA-N

物化性质

• 沸点：
  80.8±20.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  4-亚甲基-1,2-二氮杂环戊烯 生成 亚甲基环丙烷
  参考文献：
  名称：

  Chang, Moon Ho; Crawford, Robert J., Canadian Journal of Chemistry, 1981, vol. 59, p. 2556 - 2568

  摘要：

  DOI：
• 作为产物：
  描述：

  7-Methylene-3-thia-1,5-diazabicyclo<3.3.0>octane-2,4-dione 以 氘代乙腈 为溶剂， 反应 0.08h， 生成 4-亚甲基-1,2-二氮杂环戊烯
  参考文献：
  名称：

  1-Thia-3,4-diazolidine-2,5-dione functionality: a photochemical synthon for the azo group

  摘要：

  The 1-thia-3,4-diazolidine-2,5-dione functional group was shown to yield azo compounds upon photolysis. This photoreaction when combined with the known ability of this group to react in a Diels-Alder fashion or as a dinucelophile toward alkylating agents greatly increases the utility of this functionality. The dual reactivity of this group was demonstrated in the synthesis of a number of 3,4-dialkyl-1-thia-3,4-diazolidine-2,5-diones. The photolysis of these compounds produced either thermally stable cyclic azo compounds or the decomposition products of thermally unstable azo compounds.

  DOI：

  10.1021/jo00092a013

文献信息

• Theoretical and experimental study of the regioselectivity of the reaction of diazomethane with Allene
  作者：Augusto Rastelli、Marisa Bagatti、Remo Gandolfi

  DOI：10.1016/s0040-4020(01)80710-9

  日期：1994.5

  The reaction of diazomethane with allene at room temperature afforded a mixture of 4-methylene-1 -pyrazoline (1) and 3-methylene-1-pyrazoline (2) in a 93:7 ratio. This finding revises literature data which describe this reaction as regiospecific with exclusive formation of 1. Good level ab-initio calculations (e.g., HF/6-31G*//HF/6-31G*, MP4SDTQ/6-31G*//HF/6-31G* and MP4SDTQ/6-31G*//MCSCF/3-21G) qualitatively

  重氮甲烷与丙二烯在室温下反应，以93∶7的比例得到4-亚甲基-1-吡唑啉（1）和3-亚甲基-1-吡唑啉（2）的混合物。这一发现修改了文献资料，该资料将这种反应描述为具有区域特异性的反应，并且排他地形成了1。良好的从头算起（例如HF / 6-31G * // HF / 6-31G *，MP4SDTQ / 6-31G * // HF / 6-31G *和MP4SDTQ / 6-31G * // MCSCF / 3 -21G）定性地再现实验区域化学比率。
• Thermolysis of Some 4-Alkylidene-1-pyrazolines
  作者：Robert J. Crawford、Douglas M. Cameron、Hirokazu Tokunaga

  DOI：10.1139/v74-600

  日期：1974.12.15

  The thermolysis of 4-methylene-1-pyrazoline and the kinetic isotope effects of 3,3-d₂, 3,3,6,6-d₄, and 3,3,5,5,6,6-d₆ compounds were examined. Data suggest a simultaneous cleavage of both carbon–nitrogen bonds with the formation of an intermediate which by ¹³C labelling is shown to be other than the triplet planar trimethylenemethane. Product studies on 3,3-dimethyl-4-methylene-1-pyrazoline and 4-isopropylidene-1-pyrazoline are best rationalized in terms of the Chesick type intermediate.

  对4-亚甲基-1-吡唑烷进行热解，并考察了3,3-二氘、3,3,6,6-四氘和3,3,5,5,6,6-六氘化合物的动力学同位素效应。数据表明同时断裂碳氮键，形成一个中间体，通过¹³C标记表明该中间体不同于三重平面三亚甲基甲烷。对3,3-二甲基-4-亚甲基-1-吡唑烷和4-异丙基-1-吡唑烷的产物研究最好用Chesick型中间体来解释。
• Squiliacote Michael, De Felippis James, J. Org. Chem, 59 (1994) N 13, S 3564-3571
  作者：Squiliacote Michael, De Felippis James

  DOI：——

  日期：——
• Djakonow, Zhurnal Obshchei Khimii, 1945, vol. 15, p. 484
  作者：Djakonow

  DOI：——

  日期：——
• 1-Thia-3,4-diazolidine-2,5-dione functionality: a photochemical synthon for the azo group
  作者：Michael Squillacote、James De Felippis

  DOI：10.1021/jo00092a013

  日期：1994.7

  The 1-thia-3,4-diazolidine-2,5-dione functional group was shown to yield azo compounds upon photolysis. This photoreaction when combined with the known ability of this group to react in a Diels-Alder fashion or as a dinucelophile toward alkylating agents greatly increases the utility of this functionality. The dual reactivity of this group was demonstrated in the synthesis of a number of 3,4-dialkyl-1-thia-3,4-diazolidine-2,5-diones. The photolysis of these compounds produced either thermally stable cyclic azo compounds or the decomposition products of thermally unstable azo compounds.

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