Diethyl 5,5-dimethylpyrazole-3,4-dicarboxylate | 83922-91-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Diethyl 5,5-dimethylpyrazole-3,4-dicarboxylate
• 英文别名: diethyl 5,5-dimethylpyrazole-3,4-dicarboxylate
• CAS: 83922-91-2
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: UIUGGFRQHBHQJE-UHFFFAOYSA-N

物化性质

• 沸点：
  304.5±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl 5,5-dimethylpyrazole-3,4-dicarboxylate 以 乙醚 为溶剂， 以76%的产率得到3,3-Dimethyl-cycloprop-1-ene-1,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  trans-5-Palladatricyclo[4.1.0.02,4]heptanes: Complexes with monodentate, weakly coordinating ligands, formation of new derivatives and synthetic limitations

  摘要：

  The bis(acetone) complex of tetramethyl rac-3,3,7,7-tetramethyl-trans-5-palladatricyclo[4.1.0.0(2,4)]heptane-1.2,4,6-tetracarboxylate rac-1a was crystallized and investigated by X-ray structure analysis. Unlike in complexes with bidendate ligands in rac-1a.2(acetone), only a small deviation from the square planar coordination of palladium was observed. Efforts to crystallize the analogous pyridine, acetonitrile and benzonitrile complexes failed; but the labile complexes rac-1a.2([D-5]pyridine) and rac-1a. 2([D-3] acetonitrile) as well as rac-1a.2([D-6]acetone) could be characterized by H-1 and C-13 NMR spectra and a fast ligand exchange was proven by nmr. Then the ability of different 1,2-disubstituted cyclopropenes to form trans-5-pallada-tricyclo[4.1.0.0(2,4)] heptanes 1 was investigated. Only the diesters 5c-e lead to PTHs, with a diester possessing sterically demanding substituents in 3-position of the cyclopropene and with other substituents in 1- respectively 2-position of the cyclopropene either the cyclopropene-formation or the PTH-formation failed.

  DOI：

  10.1002/prac.19983400307
• 作为产物：
  描述：

  丁炔二酸二乙酯 、 2-重氮丙烷 以 乙醚 、 二氯甲烷 为溶剂， 以66%的产率得到Diethyl 5,5-dimethylpyrazole-3,4-dicarboxylate
  参考文献：
  名称：

  trans-5-Palladatricyclo[4.1.0.02,4]heptanes: Complexes with monodentate, weakly coordinating ligands, formation of new derivatives and synthetic limitations

  摘要：

  The bis(acetone) complex of tetramethyl rac-3,3,7,7-tetramethyl-trans-5-palladatricyclo[4.1.0.0(2,4)]heptane-1.2,4,6-tetracarboxylate rac-1a was crystallized and investigated by X-ray structure analysis. Unlike in complexes with bidendate ligands in rac-1a.2(acetone), only a small deviation from the square planar coordination of palladium was observed. Efforts to crystallize the analogous pyridine, acetonitrile and benzonitrile complexes failed; but the labile complexes rac-1a.2([D-5]pyridine) and rac-1a. 2([D-3] acetonitrile) as well as rac-1a.2([D-6]acetone) could be characterized by H-1 and C-13 NMR spectra and a fast ligand exchange was proven by nmr. Then the ability of different 1,2-disubstituted cyclopropenes to form trans-5-pallada-tricyclo[4.1.0.0(2,4)] heptanes 1 was investigated. Only the diesters 5c-e lead to PTHs, with a diester possessing sterically demanding substituents in 3-position of the cyclopropene and with other substituents in 1- respectively 2-position of the cyclopropene either the cyclopropene-formation or the PTH-formation failed.

  DOI：

  10.1002/prac.19983400307

文献信息

• Forrester, Alexander R.; Sadd, John S., Journal of the Chemical Society. Perkin transactions II, 1982, p. 1273 - 1278
  作者：Forrester, Alexander R.、Sadd, John S.

  DOI：——

  日期：——
• trans-5-Palladatricyclo[4.1.0.02,4]heptanes: Complexes with monodentate, weakly coordinating ligands, formation of new derivatives and synthetic limitations
  作者：A. Stephen K. Hashmi、Frank Naumann、Michael Bolte、Andreas Rivas Nass

  DOI：10.1002/prac.19983400307

  日期：——

  The bis(acetone) complex of tetramethyl rac-3,3,7,7-tetramethyl-trans-5-palladatricyclo[4.1.0.0(2,4)]heptane-1.2,4,6-tetracarboxylate rac-1a was crystallized and investigated by X-ray structure analysis. Unlike in complexes with bidendate ligands in rac-1a.2(acetone), only a small deviation from the square planar coordination of palladium was observed. Efforts to crystallize the analogous pyridine, acetonitrile and benzonitrile complexes failed; but the labile complexes rac-1a.2([D-5]pyridine) and rac-1a. 2([D-3] acetonitrile) as well as rac-1a.2([D-6]acetone) could be characterized by H-1 and C-13 NMR spectra and a fast ligand exchange was proven by nmr. Then the ability of different 1,2-disubstituted cyclopropenes to form trans-5-pallada-tricyclo[4.1.0.0(2,4)] heptanes 1 was investigated. Only the diesters 5c-e lead to PTHs, with a diester possessing sterically demanding substituents in 3-position of the cyclopropene and with other substituents in 1- respectively 2-position of the cyclopropene either the cyclopropene-formation or the PTH-formation failed.