[N'-(furfurylidene)]benzhydrazide | 62214-31-7

• 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: [N'-(furfurylidene)]benzhydrazide
• 英文别名: furfurylidene benzoylhydrazone；(E)-N'-(furan-2-yl-methylene)benzohydrazide；N-[(E)-2-furylmethyleneamino]benzamide；N-[(E)-furan-2-ylmethylideneamino]benzamide
• CAS: 62214-31-7
• 化学式: C₁₂H₁₀N₂O₂
• mdl: MFCD00447978
• 分子量: 214.224
• InChiKey: FLSCWWXUVAYOLY-UKTHLTGXSA-N

物化性质

• 沸点：
  354.35°C (rough estimate)
• 密度：
  1.2042 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [N'-(furfurylidene)]benzhydrazide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 氯仿 为溶剂， 反应 0.07h， 以96%的产率得到2-(2-呋喃基)-5-苯基-1,3,4-恶二唑
  参考文献：
  名称：

  双(三氟乙酰氧基)碘苯氧化环化芳香醛N-酰基腙

  摘要：

  摘要 芳香醛 N-酰基腙在室温下用双（三氟乙酰氧基）碘苯在 CHCl3 或 DMSO 中氧化成 2,5-二取代的 1,3,4-恶二唑，产率良好至极好。

  DOI：

  10.1080/00397910600773650
• 作为产物：
  描述：

  苯甲酸 在 硫酸 、 一水合肼 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 [N'-(furfurylidene)]benzhydrazide
  参考文献：
  名称：

  Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists

  摘要：

  Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERR alpha emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERR beta/gamma selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERR alpha agonism. We successfully engineered high affinity ERR alpha agonism into a chemical scaffold that displays selective ERR beta/gamma agonist activity (GSK4716), providing novel ERR alpha/beta/gamma pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERR alpha. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERR alpha and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1 alpha and PGC-1 beta, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.

  DOI：

  10.1016/j.bioorg.2020.104079

文献信息

• Aza-Michael Addition Reactions of Hydrazones with Activated Alkynes Catalyzed by Nitrogen-Containing Organic Bases
  作者：Zhi-Liang Yuan、Yin Wei、Min Shi

  DOI：10.1002/ejoc.201000365

  日期：2010.7

  2]-octane)-catalyzed Michael-type reactions of hydrazones with activated alkynes are described in this paper. This aza-Michael addition reaction can be applied to different types of hydrazones, such as hydrazones 1 and hydroxy-bearing hydrazones 5. The corresponding adducts are achieved in high yields under mild reaction conditions. DABCO-promoted aza-Michael addition reactions were successfully applied to

  本文描述了几种高效的 DABCO（1,4-二氮杂双环 [2.2.2]-辛烷）催化腙与活化炔烃的迈克尔型反应。这种氮杂-迈克尔加成反应可以应用于不同类型的腙，如腙1和含羟基的腙5。相应的加合物在温和的反应条件下以高产率获得。DABCO 促进的氮杂-迈克尔加成反应成功地应用于一系列具有活化炔烃的腙，以中等至良好的产率提供相应的加合物。
• Stereocontrol in Synthesis of Homoallylic Amines. Syn Selective Direct Allylation of Hydrazones with Allylboronic Acids
  作者：Arindam Das、Rauful Alam、Lars Eriksson、Kálmán J. Szabó

  DOI：10.1021/ol501699x

  日期：2014.7.18

  Allylboronic acids directly react with acyl hydrazones, affording homoallylic amine derivatives. The reaction proceeds with very high syn selectivity, which is the opposite of the stereochemistry observed for allylboration of imines. The reaction can be carried out with both aromatic and aliphatic acyl hydrazones. Based on our studies the excellent syn stereochemistry can be explained by chelation

  烯丙基硼酸直接与酰基反应，得到均烯丙基胺衍生物。该反应以非常高的顺式选择性进行，这与亚胺的烯丙基硼化所观察到的立体化学相反。该反应可以与芳族和脂肪族酰基一起进行。根据我们的研究，优异的顺式立体化学可以通过酰基和B（OH）2部分的螯合控制来解释。
• A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis:  Highly Enantioselective [3 + 2] Acylhydrazone−Enol Ether Cycloadditions
  作者：Seiji Shirakawa、Pamela J. Lombardi、James L. Leighton

  DOI：10.1021/ja052307+

  日期：2005.7.1

  A highly diastereo- and enantioselective [3 + 2] acylhydrazone-enol ether cycloaddition mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the product was obtained after recrystallization in 93% yield and 99% ee. Evidence for a stepwise mechanism and a model for the asymmetric induction

  描述了由简单的手性硅烷路易斯酸介导的高度非对映选择性和对映选择性 [3 + 2] 酰基腙烯醇醚环加成。这些反应是非常实用的，正如更大规模（5 g 腙）反应所证明的那样，其中重结晶后以 93% 的产率和 99% 的 ee 获得产物。还提供了逐步机制的证据和非对称归纳模型。
• RUBBER COMPOSITION AND PNEUMATIC TIRES
  申请人：Bridgestone Corporation

  公开号：EP0909788A1

  公开（公告）日：1999-04-21

  A rubber composition prepared by compounding 0.05 to 20 parts by weight of at least one selected from substituted hydrazide compounds represented by the following Formulas (I) to (IV) per 100 parts by weight of a rubber component comprising at least one rubber selected from the group consisting of natural rubber and synthetic rubber, and a pneumatic tire using the same: wherein A represents one selected from the group consisting of an aromatic group which may have a substituent, a hydantoin ring which may have a substituent, and a saturated or unsaturated linear hydrocarbon having 1 to 18 carbon atoms; Y represents hydrogen, an amino group, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, an alkenyl group, an aromatic group, a pyridyl group or hydrazino group; and R1 to R11 each represent hydrogen, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group or an aromatic group.

  一种橡胶组合物，其制备方法是每 100 重量份由至少一种选自天然橡胶和合成橡胶组的橡胶组成的橡胶组分中混入 0.05 至 20 重量份的至少一种选自下式(I)至(IV)所代表的取代酰肼化合物，以及使用该组合物的充气轮胎： 其中 A 代表选自芳香基团（可具有取代基）、海因环（可具有取代基）和具有 1 至 18 个碳原子的饱和或不饱和线性烃；Y 代表氢、氨基、具有 1 至 18 个碳原子的烷基、环烷基、烯基、芳香基、吡啶基或肼基；R1 至 R11 分别代表氢、具有 1 至 18 个碳原子的烷基、环烷基或芳香基。
• 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。