3-(2,2-dimethylhydrazino)cyclohex-2-en-1-one | 69948-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,2-dimethylhydrazino)cyclohex-2-en-1-one
• 英文别名: 3-(2,2-Dimethylhydrazino)-2-cyclohexen-1-on；3-(2,2-dimethylhydrazinyl)-cyclohex-2-enone；cyclohexane-1,3-dione dimethylhydrazone；1,3-cyclohexanedione-dimethylhydrazone；3-(2,2-Dimethylhydrazinyl)cyclohex-2-en-1-one
• CAS: 69948-55-6
• 化学式: C₈H₁₄N₂O
• mdl: MFCD00962356
• 分子量: 154.212
• InChiKey: JXSXSBLTWVLHOI-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  229.3±50.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,2-dimethylhydrazino)cyclohex-2-en-1-one 在 正丁基锂 、 potassium hydride 、 臭氧 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 2,2-二甲基-1,3-环己烷二酮
  参考文献：
  名称：

  Regioselective Alkylations of Cyclic 1,3-Diketonesvia Metalated Dimethylhydrazones

  摘要：

  Cyclic 1,3- diketones 1 are transformed into their 2,2-dimethylhydrazones 2, which can be alkylated regioselectively at different positions after mono-, di-, tri-, and tetrametalation. Monometalated C-2 unsubstituted hydrazones afford C-2 and N-alkylation, monometalated C-2 substituted hydrazones afford only C-2 alkylation. The regioselectivity of the alkylation of the polymetalated hydrazones follows Hauser's rule according to the sequence: NH- > C-4 Ha > C-5 > C-4 Hb. Hydrolysis of the product hydrazones 3-5 afforded mono-and polyalkylated 1,3- diketones 7 in good yields.

  DOI：

  10.1002/prac.19973390199
• 作为产物：
  描述：

  1,3-环己二酮 、 偏二甲肼 生成 3-(2,2-dimethylhydrazino)cyclohex-2-en-1-one
  参考文献：
  名称：

  Asymmetric Michael addition/lactamization via samp-/ramp-hydrazonesenantioselective synthesis of substituted tetrahydro-2,5(1H,3H)-quinolinediones

  摘要：

  DOI：

  10.1016/s0040-4039(00)96386-x

文献信息

• Synthesis of α,β-Dicarbonylhydrazones by Aerobic Manganese-Catalysed Oxidation
  作者：Carlos J. Carrasco、Francisco Montilla、Eleuterio Álvarez、Agustín Galindo

  DOI：10.1002/adsc.201800601

  日期：2018.10.4

  practical, simple, and efficient manganese‐catalysed oxidation of C(sp2)−H bond in readily available β‐carbonylenehydrazine under aerobic conditions has been developed. This protocol exhibits a wide range of functional group tolerance in β‐carbonylenehydrazines to afford α,β‐dicarbonylhydrazones. Experimental and theoretical results suggest that the reaction very likely proceeds through a radical pathway

  在有氧条件下，开发了一种实用，简单而有效的锰催化氧化法，以容易获得的β-羰基肼中的C（sp 2）-H键。该方案在β-羰基肼类化合物中具有宽泛的官能团耐受性，可提供α，β-二羰基肼类化合物。实验和理论结果表明，该反应很可能是通过Mn III物种促进的氢原子转移过程通过自由基途径进行的。
• One-pot synthesis of annulated 1,8-naphthyridines
  作者：Ivan N. Bardasov、Anastasiya U. Alekseeva、Nataliya N. Yaschenko、Svetlana V. Zhitar、Anatoliy N. Lyshchikov

  DOI：10.1515/hc-2017-0068

  日期：2017.8.28

  Abstract Annulated 1,8-naphthyridines were synthesized by one-pot reaction of aromatic aldehyde, malononitrile dimer and enehydrazinoketone.

  摘要 采用芳香醛、丙二腈二聚体和烯肼酮一锅法合成了环化1,8-萘啶化合物。
• Regioselective alkylation of dianions of cyclic 1.3-diketones via their monodimethylhydrazones. Synthesis of C-4 substituted cyclic 1.3-diketones
  作者：Ayhan S. Demir、Dieter Enders

  DOI：10.1016/s0040-4039(00)99560-1

  日期：1989.1

  Cyclic 1.3-diketones are transformed into the corresponding monodimethylhydrazones, which can be alkylated regioselectively at C-4 via dianions with various alkyl halides.

  将环状的1.3-二酮转化为相应的单二甲基azo，其可以在C-4处通过带有各种烷基卤化物的二价阴离子在区域C-4上进行区域选择性烷基化。
• Reactions of cyclic enhydrazinoketones with arylidene derivatives of malononitrile. Synthesis of fusedN-substituted 1,4-dihydropyridines
  作者：B. V. Lichitsky、V. N. Yarovenko、I. V. Zavarzin、M. M. Krayushkin

  DOI：10.1007/bf02495769

  日期：2000.7

  A new method for the synthesis of fused N-amino-1,4-dihydropyridines was proposed. The method is based on the addition of cyclic enhydrazinoketones to arylidenemalononitriles. The structures of the compounds synthesized were studied using H-1 NMR spectroscopy.
• Demir, Ayhan S.; Enders, Dieter, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 7, p. 834 - 838
  作者：Demir, Ayhan S.、Enders, Dieter

  DOI：——

  日期：——