2-furaldehyde isonicotinoylhydrazone | 6956-53-2

• 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: 2-furaldehyde isonicotinoylhydrazone
• 英文别名: (E)-N'-(furan-2-ylmethylene)isonicotinic hydrazide；(E)-N'-(furan-2-ylmethylene)isonicotinohydrazide；isonicotinic acid furfurylidenehydrazide；Isonicotinsaeure-furfurylidenhydrazid；2-furoylcarboxaldehyde isonicotinoyl hydrazone；N-Furyliden-N'-isonicotinoyl-hydrazin；N-[(E)-furan-2-ylmethylideneamino]pyridine-4-carboxamide
• CAS: 6956-53-2
• 化学式: C₁₁H₉N₃O₂
• mdl: MFCD00459302
• 分子量: 215.211
• InChiKey: OOGABHAPRCRJSP-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-furaldehyde isonicotinoylhydrazone 以 乙腈 为溶剂， 反应 0.33h， 生成 (Z)-N'-(furan-2-ylmethylene)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'-(furan-2-ylmethylene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 2.08h， 生成 2-furaldehyde 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

• Anti-infective compounds
  申请人：Brodin Priscille

  公开号：US20110178077A1

  公开（公告）日：2011-07-21

  The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及小分子化合物及其在治疗细菌感染，特别是结核病方面的用途。
• RUBBER COMPOSITION AND PNEUMATIC TIRE
  申请人：BRIDGESTONE CORPORATION

  公开号：EP1083199A1

  公开（公告）日：2001-03-14

  There are provided a rubber composition having a high modulus of elasticity and a good workability, and a pneumatic tire. A rubber composition comprising at least one of natural rubber and synthetic diene rubbers as a rubber ingredient, at least one maleimide compound, and at least one nitrogen-containing compound selected from the group consisting of polyaniline, hydrazide, and amine compound is used in a tread.

  提供了一种具有高弹性模量和良好加工性能的橡胶组合物以及一种充气轮胎。 一种橡胶组合物包含天然橡胶和合成二烯橡胶中的至少一种橡胶成分、至少一种马来酰亚胺化合物和至少一种从聚苯胺、酰肼和胺化合物组成的组中选出的含氮化合物，用于胎面。
• Sah; Peoples, Journal of the American Pharmaceutical Association (1912), 1954, vol. 43, p. 513,514
  作者：Sah、Peoples

  DOI：——

  日期：——
• Shah; Mehta; Parikh, Journal of the Indian Chemical Society, 1985, vol. 62, # 3, p. 255 - 257
  作者：Shah、Mehta、Parikh

  DOI：——

  日期：——
• Synthetic tuberculostats. V. Alkylidene derivatives of isonicotinyhydrazine
  作者：H. Herbert Fox、John T. Gibas

  DOI：10.1021/jo50014a012

  日期：1953.8

表征谱图