cyclopentane-1,3-dione dimethylhydrazone | 124015-85-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 英文名称: cyclopentane-1,3-dione dimethylhydrazone
• 英文别名: 2-Cyclopenten-1-one, 3-(2,2-dimethylhydrazino)-；3-(2,2-dimethylhydrazinyl)cyclopent-2-en-1-one
• CAS: 124015-85-6
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: WZGROPUXXIYFIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  cyclopentane-1,3-dione dimethylhydrazone 在 盐酸 、 正丁基锂 、 碘甲烷 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 0.08h， 生成 2-methyl-2-propargyl-1,3-cyclopentanedione
  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-环戊二酮 、 偏二甲肼 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以97%的产率得到cyclopentane-1,3-dione dimethylhydrazone
  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

文献信息

• 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。
• DEMIR, AYHAN S.;ENDERS, DIETER, TETRAHEDRON LETT., 30,(1989) N3, C. 1705-1708
  作者：DEMIR, AYHAN S.、ENDERS, DIETER

  DOI：——

  日期：——
• Regioselective Alkylations of Cyclic 1,3-Diketonesvia Metalated Dimethylhydrazones
  作者：Ayhan S. Demir、Dieter Enders

  DOI：10.1002/prac.19973390199

  日期：——

  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.