(Z)-N'-benzylidenebenzhydrazide | 14850-88-5

• 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: (Z)-N'-benzylidenebenzhydrazide
• 英文别名: (Z)-N'-benzylidenebenzohydrazide；N-Benzoyl-N'-benzylidenhydrazin；N-[(Z)-benzylideneamino]benzamide
• CAS: 14850-88-5
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: RISHSDLMXPLIHT-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 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：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N'-benzylidenebenzhydrazide 以 乙腈 为溶剂， 反应 3.33h， 生成 (E)-N'-benzylidenebenzohydrazide
  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：

  (E)-N'-benzylidenebenzohydrazide 以 乙腈 为溶剂， 反应 0.18h， 生成 (Z)-N'-benzylidenebenzhydrazide
  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

• Mild, Stereoselective, and Highly Efficient Synthesis of<i>N</i>-Acylhydrazones Mediated by CeCl₃·7H₂O in a Broad Range of Solvents
  作者：José Maurício dos Santos Filho

  DOI：10.1002/ejoc.201402609

  日期：2014.10

  This method uses a minimal catalytic amount of cerium(III), is stereoselective, and offers several unique features, such as compatibility with aryl, heterocyclic, alkenyl, and sensitive functional groups as well as the ability to prepare N-acylhydrazones from highly hindered substrates. More strikingly, cerium(III) efficiently mediated the reaction with less reactive substrates such as diaryl and alkyl

  在一种温和而实用的方法中，酰肼和醛在氯化铈 (III) 介导下发生缩合反应，迅速转化为 N-酰基腙。该方法使用最低催化量的铈 (III)，具有立体选择性，并提供了几个独特的功能，例如与芳基、杂环、烯基和敏感官能团的相容性以及从高度受阻的底物制备 N-酰基腙的能力. 更引人注目的是，当没有催化剂的经典方案无效时，铈 (III) 可以有效地介导与反应性较低的底物（如二芳基和烷基芳基酮）的反应。该方法能够合成结构多样的 N-酰基腙库，这些库在合成和药物化学中具有应用。
• MANDELIC HYDRAZIDES
  申请人：Gericke Rolf

  公开号：US20090221712A1

  公开（公告）日：2009-09-03

  Novel mandelic hydrazides of the formula (I), in which R 1 -R 11 have the meanings indicated in claim 1, are SGK inhibitors and can be used for the treatment of SGK-induced diseases and complaints, such as diabetes, obesity, metabolic syndrome (dyslipidaemia), systemic and pulmonary hypertonia, cardiovascular diseases and kidney diseases, generally in fibroses and inflammatory processes of any type.

  式(I)中的新颖杏仁酸肼化合物，其中R1-R11具有权利要求1中指示的含义，是SGK抑制剂，可用于治疗SGK诱导的疾病和症状，如糖尿病、肥胖、代谢综合征（血脂异常）、全身和肺动脉高压、心血管疾病和肾脏疾病，一般在任何类型的纤维化和炎症过程中。
• [EN] THE EXOCYST AS A NOVEL DRUG TARGET OF ENDOSIDIN2 AND APPLICATION AS A THERAPEUTIC<br/>[FR] L'EXOKYSTE EN TANT QUE NOUVELLE CIBLE DE MÉDICAMENT DE L'ENDOSIDINE-2 ET APPLICATION THÉRAPEUTIQUE
  申请人：UNIV CALIFORNIA

  公开号：WO2017049016A1

  公开（公告）日：2017-03-23

  A method of altering exocytosis in a plant or animal cell is provided. The method includes exposing the cell to a compound that binds to an EXO70 protein isoform. Also provided is a method of treating diabetes or cancer in a subject in need thereof, which includes administering to the subject an effective amount of a compound that binds to an EXO70 protein isoform. In addition, a method of screening for a substance that alters exocytosis in a plant or animal cell is provided, and analogs of compound Endosidin2 are also provided.

  提供了一种改变植物或动物细胞外排分泌的方法。该方法包括将细胞暴露于结合到EXO70蛋白同工型的化合物中。还提供了一种治疗糖尿病或癌症的方法，包括向需要的受试者施用结合到EXO70蛋白同工型的化合物的有效量。此外，还提供了一种筛选能够改变植物或动物细胞外排分泌的物质的方法，并且还提供了化合物Endosidin2的类似物。
• Synthesis of 1,3-Disubstituted <i>N</i>-Amino-1,2,3,4-tetrahydroisoquinolines
  作者：Kang Zhao、Li Zhang、Xiu-Fang Zheng、Gregory Linn

  DOI：10.1055/s-2007-967948

  日期：2007.2

  The synthesis of 1,3-disubstituted N-amino-1,2,3,4-tetrahydroisoquinolines from the corresponding hydrazide intermediate via Pictet-Spengler reaction is described and the effect of the aldehyde on the stereoconfiguration of the products is discussed.

  描述了通过Pictet-Spengler反应从相应的酰肼中间体合成1,3-二取代的N-氨基-1,2,3,4-四氢异喹啉的过程，并讨论了醛对产物立体构型的影响。
• Analogs of Nitrofuran Antibiotics to Combat Resistance
  申请人：The Trustees of Indiana University

  公开号：US20220009914A1

  公开（公告）日：2022-01-13

  Novel compounds and methods of killing or inhibiting the growth of bacteria.

  小说化合物及杀死或抑制细菌生长的方法。