3,4,5-trimethoxybenzaldehyde N-[-(3,4,5-trimethoxyphenyl)methylidene]hydrazone | 7251-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4,5-trimethoxybenzaldehyde N-[-(3,4,5-trimethoxyphenyl)methylidene]hydrazone
• 英文别名: 3.4.5-Trimethoxy-benzaldazin；bis-(3,4,5-trimethoxy-benzylidene)-hydrazine；Bis-(3,4,5-trimethoxy-benzyliden)-hydrazin；1,2-Bis(3,4,5-trimethoxybenzylidene)hydrazine；1-(3,4,5-trimethoxyphenyl)-N-[(3,4,5-trimethoxyphenyl)methylideneamino]methanimine
• CAS: 7251-01-6
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: DDYCVNVXONZPBT-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C
• 沸点：
  502.4±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxybenzaldehyde N-[-(3,4,5-trimethoxyphenyl)methylidene]hydrazone 在 poly(diselanediyl-1,2-phenylene) 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 以33%的产率得到3,4,5-三甲氧基苯甲酸
  参考文献：
  名称：

  ONE-POT OXIDATION OF AZOMETHINE COMPOUNDS INTO ARENECARBOXYLIC ACIDS

  摘要：

  Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.

  DOI：

  10.1081/scc-100105891
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 一水合肼 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3,4,5-trimethoxybenzaldehyde N-[-(3,4,5-trimethoxyphenyl)methylidene]hydrazone
  参考文献：
  名称：

  2,2-二甲基-1,3-二恶烷-4,6-二酮的甲氧基亚苄基衍生物及其饱和类似物与某些亲核试剂的反应

  摘要：

  实现了2,2-二甲基-1,3-二恶烷-4,6-二酮的甲氧基亚苄基衍生物及其饱和类似物与氢氧化钾在甲醇，氨和水合肼中的反应。制备并表征了适合用作合成基于它们的各种结构的结构嵌段的甲氧基亚苄基-丙二酸的1,2-双（甲氧基亚苄基）肼，酰胺和酰肼。

  DOI：

  10.1007/s10593-011-0690-7

文献信息

• A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes
  作者：Bo Jiang、Wen-Juan Hao、Jin-Peng Zhang、Shu-Jiang Tu、Feng Shi

  DOI：10.1039/b822645h

  日期：——

  A new domino autocatalytic reaction of imines with Meldrum's acid was described. In this reaction, a series of polycyclic spiro[5.5]undecane-1,5,9-trione and dispiro[4.2.5.2]pentadecane-9,13-dione derivatives, with remarkable diastereoselectivity, were successfully synthesized in acidic condition, and up to six new bonds were formed accompanied by the CN bond cleavage of the imines and the decomposition of Meldrum's acid, with by-product of acetohydrazide as a novel autocatalyst.

  描述了一种新颖的烯胺与梅尔德鲁姆酸的多米诺自催化反应。在这一反应中，在酸性条件下成功合成了一系列具有显著非对映选择性的多环螺[5.5]十一烷-1,5,9-三酮和双螺[4.2.5.2]十五烷-9,13-二酮衍生物，最多形成六个新键，同时伴随着烯胺的CN键断裂和梅尔德鲁姆酸的分解，副产物乙酰肼作为新型自催化剂。
• Reactions of methoxybenzylidene derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione and their saturated analogs with certain nucleophilic reagents
  作者：Z. Tetere、I. Ravina、I. Rijkure、D. Zicane

  DOI：10.1007/s10593-011-0690-7

  日期：2011.3

  The reactions of the methoxybenzylidene derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione and their saturated analogs with potassium hydroxide in methanol, ammonia, and hydrazine hydrate were realized. The 1,2-bis(methoxybenzylidene)hydrazines, amides, and hydrazides of methoxybenzylidene-malonic acid, suitable for use as structural blocks in the synthesis of various structures based on them, were

  实现了2,2-二甲基-1,3-二恶烷-4,6-二酮的甲氧基亚苄基衍生物及其饱和类似物与氢氧化钾在甲醇，氨和水合肼中的反应。制备并表征了适合用作合成基于它们的各种结构的结构嵌段的甲氧基亚苄基-丙二酸的1,2-双（甲氧基亚苄基）肼，酰胺和酰肼。
• Pietra; Trinchera, Gazzetta Chimica Italiana, 1956, vol. 86, p. 1045,1050
  作者：Pietra、Trinchera

  DOI：——

  日期：——
• An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound
  作者：Khalid M. Khan、Waqas Jamil、Nida Ambreen、Muhammad Taha、Shahnaz Perveen、Guillermo A. Morales

  DOI：10.1016/j.ultsonch.2013.12.011

  日期：2014.5

  Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating. (C) 2013 Elsevier B.V. All rights reserved.
• Buu-Hoi,N.P.; Saint-Ruf,G., Bulletin de la Societe Chimique de France, 1967, p. 955 - 960
  作者：Buu-Hoi,N.P.、Saint-Ruf,G.

  DOI：——

  日期：——