N’-(benzo[b][1,3]dioxol-5-ylmethylidene)-2-hydroxybenzohydrazide | 100880-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N’-(benzo[b][1,3]dioxol-5-ylmethylidene)-2-hydroxybenzohydrazide
• 英文别名: ST033341；N-(1,3-benzodioxol-5-ylmethylideneamino)-2-hydroxybenzamide
• CAS: 100880-98-6
• 化学式: C₁₅H₁₂N₂O₄
• mdl: MFCD00515240
• 分子量: 284.271
• InChiKey: XSOVDKJJBAEXAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N’-(benzo[b][1,3]dioxol-5-ylmethylidene)-2-hydroxybenzohydrazide 、 巯基乙酸 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以55%的产率得到N-(2-(benzo[d][1,3]dioxol-5-yl)-4-oxothiazolidin-3-yl)-2-hydroxybenzamide
  参考文献：
  名称：

  Synthesis and Biological Activity of 2-Hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamide

  摘要：

  2-Hydroxy benzoic acid hydrazide (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding 2-hydroxy benzoic acid arylidene hydrazides (2a-h) in good yields. Cyclocondensation of compounds 2a-h with thioglycolic acid yields 2-hydroxy-N(4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (3a-h). These 3a-h compounds are for the reacted with benzaldehyde in the presence of sodium ethanolate affords, giving 2-hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (4a-h). The structures of these compounds were established on the basis of analytical and spectral data. All the newly synthesized compounds were evaluated for their antibacterial and antifungal activities. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903176521
• 作为产物：
  描述：

  胡椒醛 、 水杨酰肼 在 水 、 溶剂黄146 作用下， 以 neat (no solvent) 为溶剂， 反应 0.03h， 以95%的产率得到N’-(benzo[b][1,3]dioxol-5-ylmethylidene)-2-hydroxybenzohydrazide
  参考文献：
  名称：

  立体选择性，无溶剂，高效利用砂轮化学合成醛基和酮基N-酰基hydr

  摘要：

  已经开发出了温和而有效的N-酰基hydr酮合成方法，该方法采用了简单的磨石程序，从而产生了51个实例，这些实例均显示出多种结构特征，其中21个实例首次在本文中进行了描述。该方法在室温下在乙酸催化下无需任何有机溶剂即可工作，可促进形成基本纯净的粗产物，并避免繁琐的后处理和有害溶剂的使用以及能耗。另外，如NMR分析所支持的，其导致N-酰基hydr的立体选择性形成。

  DOI：

  10.1039/c7gc00730b

文献信息

• Stereoselective, solvent free, highly efficient synthesis of aldo- and keto-N-acylhydrazones applying grindstone chemistry
  作者：José Maurício dos Santos Filho、Savio Moita Pinheiro

  DOI：10.1039/c7gc00730b

  日期：——

  A mild and efficient synthesis of N-acylhydrazones has been developed, applying a simple grindstone procedure, leading to a library of 51 examples exhibiting a broad variety of structural features, 21 of them described for the first time in this paper. This methodology works without any organic solvent under the catalysis of acetic acid at room temperature, promotes the formation of essentially pure

  已经开发出了温和而有效的N-酰基hydr酮合成方法，该方法采用了简单的磨石程序，从而产生了51个实例，这些实例均显示出多种结构特征，其中21个实例首次在本文中进行了描述。该方法在室温下在乙酸催化下无需任何有机溶剂即可工作，可促进形成基本纯净的粗产物，并避免繁琐的后处理和有害溶剂的使用以及能耗。另外，如NMR分析所支持的，其导致N-酰基hydr的立体选择性形成。
• Synthesis and Biological Activity of 2-Hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamide
  作者：Hasmukh S. Patel、Sumeet J. Patel

  DOI：10.1080/10426500903176521

  日期：2010.7.30

  2-Hydroxy benzoic acid hydrazide (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding 2-hydroxy benzoic acid arylidene hydrazides (2a-h) in good yields. Cyclocondensation of compounds 2a-h with thioglycolic acid yields 2-hydroxy-N(4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (3a-h). These 3a-h compounds are for the reacted with benzaldehyde in the presence of sodium ethanolate affords, giving 2-hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (4a-h). The structures of these compounds were established on the basis of analytical and spectral data. All the newly synthesized compounds were evaluated for their antibacterial and antifungal activities. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.