3,4,5-trimethoxybenzaldehyde isonicotinoylhydrazone | 67837-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,4,5-trimethoxybenzaldehyde isonicotinoylhydrazone
• 英文别名: (E)-N'-(3,4,5-trimethoxybenzylidene)isonicotinic hydrazide；(E)-N'-(3,4,5-trimethoxybenzylidene)isonicotinohydrazide；N'-[(E)-(3,4,5-trimethoxyphenyl)methylidene]pyridine-4-carbohydrazide；N-[(E)-(3,4,5-trimethoxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 67837-40-5
• 化学式: C₁₆H₁₇N₃O₄
• 分子量: 315.329
• InChiKey: QXLMRSDBFLKAPR-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxybenzaldehyde isonicotinoylhydrazone 以 乙腈 为溶剂， 反应 0.17h， 生成 (Z)-N'-(3,4,5-trimethoxybenzylidene)isonicotinic hydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  (Z)-N'-(3,4,5-trimethoxybenzylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 1.0h， 生成 3,4,5-trimethoxybenzaldehyde isonicotinoylhydrazone
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519

文献信息

• Malhotra, Manav; Sharma, Gaurav; Deep, Aakash, Acta poloniae pharmaceutica, 2012, vol. 69, # 4, p. 637 - 644
  作者：Malhotra, Manav、Sharma, Gaurav、Deep, Aakash

  DOI：——

  日期：——
• 2,3-Dimethoxybenzaldehyde isonicotinoylhydrazone chloroform monosolvate, and the mono- and dihydrates of 3,4,5-trimethoxybenzaldehyde isonicotinoylhydrazone: hydrogen-bonded supramolecular structures in one, two and three dimensions
  作者：Monica A. Peralta、Marcus N. V. de Souza、Solange M. S. V. Wardell、James L. Wardell、John N. Low、Christopher Glidewell

  DOI：10.1107/s0108270106052486

  日期：2007.1.15

  In 2,3-dimethoxybenzaldehyde isonicotinoylhydrazone chloroform monosolvate, C15H15N3O3 center dot CHCl3, the hydrazone molecules are linked by a combination of N-H center dot center dot center dot N and C-H center dot center dot center dot N hydrogen bonds into chains from which the chloroform molecules are pendent. 3,4,5-Trimethoxybenzaldehyde isonicotinoylhydrazone forms two stoichiometric hydrates. In the monohydrate, C16H17N3O4 center dot H2O, the components are linked into sheets by a combination of O-H center dot center dot center dot O, O-H center dot center dot center dot N and N-H center dot center dot center dot N hydrogen bonds, and in the dihydrate, C16H17N3O4 center dot 2H(2)O, a combination of O-H center dot center dot center dot O, O-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds links the components into a three-dimensional framework structure.
• Acylhydrazones as Widely Tunable Photoswitches
  作者：Derk Jan van Dijken、Petr Kovaříček、Svante P. Ihrig、Stefan Hecht

  DOI：10.1021/jacs.5b09519

  日期：2015.12.2

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.