(E)-N'-(1-(thiophen-2-yl)ethylidene)benzohydrazide | 113875-20-0

• 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: (E)-N'-(1-(thiophen-2-yl)ethylidene)benzohydrazide
• 英文别名: (E)-N'-[1-(thiophen-2-yl)ethylidene]benzohydrazide；(E)-N'-(1-(thiophen-2-yl)ethylidene)benzhydrazide；benzoic acid (1-thiophen-2-ylethylidene)hydrazide；thiophene-2-methylketone benzoylhydrazone；benzoic acid-(1-[2]thienyl-ethylLiDenehydrazide)；Benzoesaeure-(1-[2]thienyl-aethylidenhydrazid)；N'-[(1E)-1-(thiophen-2-yl)ethylidene]benzohydrazide；N-[(E)-1-thiophen-2-ylethylideneamino]benzamide
• CAS: 113875-20-0
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: FDMVTSJWRWLLPM-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (E)-N'-(1-(thiophen-2-yl)ethylidene)benzohydrazide 生成 (Z)-N'-(1-(thiophen-2-yl)ethylidene)benzhydrazide
  参考文献：
  名称：

  有机化合物及其制备方法、显示基板和显示装置

  摘要：

  公开一种有机化合物及其制备方法、显示基板和显示装置，涉及显示技术领域，用于提高显示装置的显示效果与使用寿命。该有机化合物的结构式如下式(I)所示：

  公开号：

  CN114369059A
• 作为产物：
  描述：

  (Z)-N'-(1-(thiophen-2-yl)ethylidene)benzhydrazide 以 乙腈 为溶剂， 反应 4.17h， 生成 (E)-N'-(1-(thiophen-2-yl)ethylidene)benzohydrazide
  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

• Stereoselective, solvent free, highly efficient synthesis of aldo- and keto-N-acylhydrazones applying grindstone chemistry
  作者：José Maurício dos Santos Filho、Savio Moita Pinheiro

  DOI：10.1039/c7gc00730b

  日期：——

  A mild and efficient synthesis of N-acylhydrazones has been developed, applying a simple grindstone procedure, leading to a library of 51 examples exhibiting a broad variety of structural features, 21 of them described for the first time in this paper. This methodology works without any organic solvent under the catalysis of acetic acid at room temperature, promotes the formation of essentially pure

  已经开发出了温和而有效的N-酰基hydr酮合成方法，该方法采用了简单的磨石程序，从而产生了51个实例，这些实例均显示出多种结构特征，其中21个实例首次在本文中进行了描述。该方法在室温下在乙酸催化下无需任何有机溶剂即可工作，可促进形成基本纯净的粗产物，并避免繁琐的后处理和有害溶剂的使用以及能耗。另外，如NMR分析所支持的，其导致N-酰基hydr的立体选择性形成。
• 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。
• Enantioselective Allylation of Ketone-Derived Benzoylhydrazones:  Practical Synthesis of Tertiary Carbinamines
  作者：Richard Berger、Keiko Duff、James L. Leighton

  DOI：10.1021/ja0486418

  日期：2004.5.1

  A highly practical method for the enantioselective allylation of ketone-derived benzoylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of benzoylhydrazones to give the hydrazide products with good to excellent enantioselectivity (84-97% ee). A mechanism in which the acylhydrazone becomes caovalently attached to the silane has been established

  已经开发了一种用于酮衍生的苯甲酰腙的对映选择性烯丙基化的非常实用的方法。先前报道的应变硅环试剂 1 与多种苯甲酰腙反应，得到具有良好至优异对映选择性 (84-97% ee) 的酰肼产物。已经建立了酰基腙与硅烷共价连接的机制。
• Synthesis, characterization and magnetic properties of mono- and dinuclear complexes of Manganese (III) and (IV) supported by (E)-N′-(1-(thiophene-2-yl)ethylidene)benzohydrazide arising from an unusual Mn(III) to Mn(IV) disproportionation reaction
  作者：David Specklin、Clarisse Tourbillon、Vitor Rosa、Mohamedally Kurmoo、Richard Welter

  DOI：10.1016/j.inoche.2012.03.001

  日期：2012.6

  Abstract A new MnIV dinuclear complex [MnIV2(μ-O)2(L′)4].2CH3OH (HL′ = (E)-N′-(1-(thiophen-2-yl)ethylidene)benzohydrazide) was obtained from MnIII(acetate)3.2H2O by an unusual MnIII disproportionation reaction. This compound exhibits a strong antiferromagnetic coupling with a J value of − 149(5) cm− 1. Moreover, a new MnIII mononuclear complex bearing L′ named [MnIII(acac)(L′)2] (acac = acetylacetonate)

  摘要 一种新的 MnIV 双核络合物 [MnIV2(μ-O)2(L')4].2CH3OH (HL' = (E)-N'-(1-(thiophen-2-yl)ethylidene)benzohydrazide) 从MnIII(acetate)3.2H2O 通过不寻常的 MnIII 歧化反应生成。该化合物表现出强反铁磁耦合，J值为−149(5) cm−1。此外，获得了一种新的带有L'的MnIII单核复合物，名为[MnIII(acac)(L')2]（acac = 乙酰丙酮）来自 [MnIII(acac)3] 并被描述为围绕具有磁性的锰配合物的系统研究工作的一部分。
• Recyclable gold(I)-catalyzed hydrohydrazidation of terminal alkynes towards keto-N-acylhydrazones
  作者：Siqi Liu、Jianying Li、Wenli Hu、Bin Huang、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2022.122411

  日期：2022.9

  heterogeneous gold(I)-catalyzed hydrohydrazidation of terminal alkynes with diverse hydrazides has been developed in chlorobenzene at 60 °C by using an MCM-41-immobilized diphenylphosphine gold(I) complex [Ph2P-MCM-41-AuNTf2] as the catalyst, providing a novel and practical method for the synthesis of a wide variety of substituted keto-N-acylhydrazones in good to excellent yields. This heterogenized gold(I) catalyst

  使用 MCM-41 固定的二苯基膦金 (I) 配合物 [Ph 2 P-MCM-41 ，在 60 °C 的氯苯中，开发了一种简便高效的非均相金 (I) 催化的末端炔烃与多种酰肼的加氢反应。-AuNTf 2 ] 作为催化剂，为合成多种取代的酮基-N-酰基腙提供了一种新颖实用的方法，产率从良好到优异。这种异质化的金 (I) 催化剂也很容易通过过滤反应混合物来回收，并且可以回收多达八次，而没有任何明显的催化效率损失。