2-acetylfuran carbethoxyhydrazon | 22589-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-acetylfuran carbethoxyhydrazon
• 英文别名: 2-acetylfuran carboethoxyhydrazone；Hydrazinecarboxylic acid, [1-(2-furanyl)ethylidene]-, ethyl ester；ethyl N-[1-(furan-2-yl)ethylideneamino]carbamate
• CAS: 22589-74-8
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: PSQVEVMYYAVIDQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetylfuran carbethoxyhydrazon 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以39%的产率得到4-(furan-2-yl)-1,2,3-thiadiazole
  参考文献：
  名称：

  Synthesis of 2- and 3-acetylfuran carbethoxyhydrazones and investigation of their reaction with thionyl chloride

  摘要：

  By the reaction of 2- and 3-acetylfurans with ethoxycarbonyl hydrazine in presence of acetic acid a series of carboethoxyhydrazones was synthesized. On the basis of the H-1 NMR spectra it was shown that in the compounds obtained furyl substituent and ethoxycarbonyl group might be located both in Z- and in E-position with respect to the C=N bond. The isomer ratio for various types of substitution in the furan ring was established. It was shown that the introduction of two methyl groups in the positions adjacent to the hydrazone group leads to thermal lability of the corresponding hydrazone. 2-Acetyl-, 5-methyl-2-acetyl-, and 3-acetylfuran carbethoxyhydrazones under the action of thionyl chloride undergo cyclization to 4-furyl-1,2,3-thiadiazoles. In the case of 3-methyl-5-acetyl- and 2-methyl-3-acetylfuran a mixture of corresponding thiadiazoles and the products of chlorination of carbethoxyhyrazone fragment was formed. It was shown that the introduction of methyl group in the furan ring leads to thermal lability of furylthiadiazoles.

  DOI：

  10.1134/s1070363215010119
• 作为产物：
  描述：

  2-乙酰基呋喃 、 肼基甲酸乙酯 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.17h， 以75%的产率得到2-acetylfuran carbethoxyhydrazon
  参考文献：
  名称：

  Synthesis of 2- and 3-acetylfuran carbethoxyhydrazones and investigation of their reaction with thionyl chloride

  摘要：

  By the reaction of 2- and 3-acetylfurans with ethoxycarbonyl hydrazine in presence of acetic acid a series of carboethoxyhydrazones was synthesized. On the basis of the H-1 NMR spectra it was shown that in the compounds obtained furyl substituent and ethoxycarbonyl group might be located both in Z- and in E-position with respect to the C=N bond. The isomer ratio for various types of substitution in the furan ring was established. It was shown that the introduction of two methyl groups in the positions adjacent to the hydrazone group leads to thermal lability of the corresponding hydrazone. 2-Acetyl-, 5-methyl-2-acetyl-, and 3-acetylfuran carbethoxyhydrazones under the action of thionyl chloride undergo cyclization to 4-furyl-1,2,3-thiadiazoles. In the case of 3-methyl-5-acetyl- and 2-methyl-3-acetylfuran a mixture of corresponding thiadiazoles and the products of chlorination of carbethoxyhyrazone fragment was formed. It was shown that the introduction of methyl group in the furan ring leads to thermal lability of furylthiadiazoles.

  DOI：

  10.1134/s1070363215010119

文献信息

• Preparation of 2<i>H</i>-spiro[benzo[<i>d</i>]isothiazole-3,3′-pyrazole]-1, 1-dioxide-2′(4′<i>H</i>)-carboxylates from dilithiated<i>C</i>(α),<i>N</i>-carboalkoxyhydrazones and methyl 2-(aminosulfonyl)benzoate
  作者：Anna C. Dawsey、Chandra Potter、John D. Knight、Zachary C. Kennedy、Ellyn A. Smith、Amanda M. Acevedo-Jake、Andrew J. Puciaty、Clyde R. Metz、Charles F. Beam、William T. Pennington、Donald G. VanDerveer

  DOI：10.1002/jhet.50

  日期：2009.3

  A variety of substituted spiro(benzoisothiazole-pyrazoles) have been prepared by the condensation of dilithiated C(α),N-carboalkoxyhydrazones with lithiated methyl 2-(aminosulfonyl)benzoate followed by the cyclization of intermediates with acetic anhydride, which also resulted in spiro N-acetylated products when carbomethoxyhydrazones or carboethoxyhydrazones were used, and spiro NH products when

  通过将二锂化的C（α），N-羰基烷氧基azo与锂化的2-（氨基磺酰基）苯甲酸甲酯缩合，然后用乙酸酐环化中间体，制得了各种取代的螺（苯并异噻唑-吡唑）。当使用碳甲氧基hydr或碳乙氧基hydr时，N-乙酰化产物；当使用碳-叔丁氧基hydr时，螺为NH产物。杂环化学杂志，46，231（2009）。