(E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)isonicotinic hydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)isonicotinic hydrazide
• 英文别名: (E)-N′-(3,4-dihydronaphthalen-1(2H)-ylidene)isonicotinohydrazide；N-[(E)-3,4-dihydro-2H-naphthalen-1-ylideneamino]pyridine-4-carboxamide
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: GMDKQURESIYJPK-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.13h， 生成 (Z)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)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-dihydronaphthalen-1(2H)-ylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.42h， 生成 (E)-N'-(3,4-dihydronaphthalen-1(2H)-ylidene)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

文献信息

• Synthesis, characterization and biological applications of new copper(II) complexes of aryl hydrazones
  作者：Kiran Tummalapalli、Vasavi C. S.、Punnagai Munusami、Madhvesh Pathak、Balamurali M. M.

  DOI：10.1002/aoc.3680

  日期：2017.8

  tetra‐coordination in all the mononuclear crystalline complexes with high thermal stability. Further, significant interaction of these novel complexes with calf thymus DNA via intercalative mode of binding was revealed by electronic absorption spectroscopy. The chemical nuclease activity of the complexes on pBR322 DNA was investigated in the presence and absence of oxidizing agent (H2O2). A potent nuclease activity

  用芳基配体处理乙酸铜（II）后，以可观的收率生产了四种新的铜（II）固体衍生物。各种表征技术，包括红外，紫外可见光，NMR，电子顺磁共振和质谱，元素分析，扫描电子显微镜，粉末X射线衍射和热重分析，揭示了所有具有高热稳定性的单核晶体配合物中的四配位。此外，通过电子吸收光谱揭示了这些新颖复合物通过结合的结合模式与小牛胸腺DNA的显着相互作用。在存在和不存在氧化剂（H 2 O 2）的情况下，研究了复合物对pBR322 DNA的化学核酸酶活性。）。仅在H 2 O 2存在下才观察到有效的核酸酶活性。此外，对新配体和复合物的抗菌和抗真菌研究表明，后者具有相对较好的活性。
• US9168268B1
  申请人：——

  公开号：US9168268B1

  公开（公告）日：2015-10-27
• 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.