cinnamaldehyde benzoylhydrazone | 372959-92-7

• 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: cinnamaldehyde benzoylhydrazone
• 英文别名: (E)-N'-((E)-3-phenylallylidene)benzohydrazide；N'-((1E,2E)-3-phenylallylidene)benzohydrazide；N’-((1E,2E)-3-phenylallylidene)benzohydrazide；N'-[(1E,2E)-3-phenyl-2-propenylidene]benzohydrazide；N-[(E)-[(E)-3-phenylprop-2-enylidene]amino]benzamide
• CAS: 372959-92-7
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: IBLXLVVKHVGRSI-UVZCHINQSA-N

物化性质

• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 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：

  cinnamaldehyde benzoylhydrazone 以 phosphate buffer 、 乙醇 为溶剂， 生成 苯甲酰肼
  参考文献：
  名称：

  通过可逆的形成来控制挥发性醛和酮的释放-经典“香精”正在发展。

  摘要：

  发现通过在水中可逆地形成芳香醛和/或酮与酰肼的共价酰基obtained形成的动态混合物是用于控制释放高挥发性有机分子的有效递送系统。

  DOI：

  10.1039/b602312f
• 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 cinnamaldehyde benzoylhydrazone
  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

• One-Pot Tandem 1,4- and 1,2-Addition of Phosphites to α,β-Unsaturated Hydrazones
  作者：Christian Stevens、Ellen Van Meenen、Kurt Masschelein、Kristof Moonen、Ann De Blieck、Jozef Drabowicz

  DOI：10.1055/s-2007-986654

  日期：2007.10

  The 1,4- and 1,2-addition of phosphites to α,β-unsaturated hydrazones was investigated. When silylated phosphites and trialkyl phosphites were compared, trialkyl phosphites gave better conversions and subsequently higher yields. A variety of hydrazones were evaluated as substrate in this reaction, which yield 3-phosphonyl-1-hydrazinoalkyl phosphonates.

  探讨了膦酸酯对α,β-不饱和腙的1,4-和1,2-加成反应。对比了甲硅烷基化膦酸酯和三烷基膦酸酯的效果，结果表明三烷基膦酸酯的转化率更高，从而获得了更高的产率。在该反应中评估了多种腙作为底物，最终产物为3-膦酰基-1-肼基烷基膦酸酯。
• Lewis Acid-Catalyzed Allylation Reactions of Acylhydrazones with Tetraallyltin in Aqueous Media
  作者：Shū Kobayashi、Tomoaki Hamada、Kei Manabe

  DOI：10.1055/s-2001-15166

  日期：——

  Allylation reactions of various benzoylhydrazones with tetraallyltin were found to proceed smoothly in the presence of scandium triflate as a Lewis acid catalyst at ambient temperature in aqueous media, to afford the corresponding homoallylic amine derivatives in high yields. Three-component reactions of aldehydes, benzoylhydrazine, and tetraallyltin were also catalyzed by scandium triflate in the same media. Furthermore, a simple procedure to prepare oxazolidinone derivatives utilizing these reactions was developed.

  在水相介质中，在三氟甲磺酸钪作为路易斯酸催化剂的存在下，多种苯甲酰肼与四烯基锡的烯化反应在室温下顺利进行，以高产率生成相应的同烯丙基胺衍生物。醛、苯甲酰肼和四烯基锡的三组分反应也可以在相同介质中通过三氟甲磺酸钪催化。此外，还开发了一种利用这些反应制备恶唑啉酮衍生物的简单方法。
• [EN] USE OF DYNAMIC MIXTURES FOR A CONTROLLED RELEASE OF FRAGRANCES<br/>[FR] UTILISATION DE MELANGES DYNAMIQUES POUR LIBERATION CONTROLEE DE FRAGRANCES
  申请人：FIRMENICH & CIE

  公开号：WO2006016248A1

  公开（公告）日：2006-02-16

  The present invention relates to a delivery system in the form of a dynamic mixture obtained by reacting together, in the presence of water, at least one hydrazine derivative with at least one perfuming, flavoring, insect repellent or attractant, bactericide and/or fungicide aldehyde or ketone. The invention's mixture is capable of releasing in a controlled and prolonged manner said aldehyde or ketone in the surrounding environment. Furthermore, the present invention concerns also the use of said dynamic mixtures as perfuming ingredients as well as the perfuming compositions or perfumed articles comprising the invention's mixtures.

  本发明涉及一种交互反应得到的动态混合物形式的递送系统，所述动态混合物是通过在水的存在下，将至少一种肼衍生物与至少一种香料、调味剂、驱虫剂或诱引剂、杀菌剂和/或杀菌醛或酮一起反应而获得的。本发明的混合物能够在周围环境中以受控和持久的方式释放所述的醛或酮。此外，本发明还涉及将所述动态混合物用作香料成分，以及包含本发明混合物的香水组合物或香水制品的用途。
• Process for producing 1-acyl-2-pyrazoline derivative
  申请人：Mitsui Toatsu Chemicals, Inc.

  公开号：US04895947A1

  公开（公告）日：1990-01-23

  1-Acyl-2-pyrazoline derivatives represented by the formula ##STR1## where R.sup.1 denotes a hydrogen atom, pyridyl group, pyrazinyl group, alkyl group, aryl group, or alkoxy group; and R.sup.2, R.sup.3, and R.sup.4 independently denote a hydrogen atom, furyl group, pyridyl group, alkyl group, or aryl group, are produced by cyclizing by heating an acylhydrazone derivative represented by the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are defined as above, to produce compounds having useful anti-cerebral edema activity.

  1-酰基-2-吡唑啉衍生物由以下式表示##STR1##其中R.sup.1表示氢原子、吡啶基、吡嗪基、烷基、芳基或烷氧基；R.sup.2、R.sup.3和R.sup.4独立地表示氢原子、呋喃基、吡啶基、烷基或芳基；通过加热表示为以下式的酰基腙衍生物进行环化合成，其中R.sup.1、R.sup.2、R.sup.3和R.sup.4如上定义，以产生具有有用的抗脑水肿活性的化合物。
• 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。