反式-N-(4-(3-氧代-3-苯基-1-丙烯基)苯基)乙酰胺 | 102059-18-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 反式-N-(4-(3-氧代-3-苯基-1-丙烯基)苯基)乙酰胺
• 英文名称: N-{4-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]phenyl}acetamide
• 英文别名: N-[4-(3-oxo-3-phenyl-propenyl)-phenyl]-acetamide；4-acetamido-(E)-chalcone；4-acetylamino-trans-chalcone；4-Acetamino-trans-chalkon；(E)-3-(4-acetamidophenyl)-1-phenyl-2-propen-1-one；4-Acetamidochalcone；N-[4-[(E)-3-oxo-3-phenylprop-1-enyl]phenyl]acetamide
• CAS: 102059-18-7
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: MJYUMWOKEJNYEM-FMIVXFBMSA-N

物化性质

• 沸点：
  501.5±50.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-N-(4-(3-氧代-3-苯基-1-丙烯基)苯基)乙酰胺 在 氢氧化钾 、 二乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  A Modular Synthesis of Unsymmetrical Tetraarylazadipyrromethenes

  摘要：

  A stepwise route to unsymmetrical tetraarylazadipyrromethenes by a condensation of 2,4-diaryl-5-nitroso-pyrroles with 2,4-diarylpyrroles is described. This modular building-block approach allows for the introduction of up to four different aryl substituents on the azadipyrromethene and is tolerant of a varied substituent set. An efficient synthesis of the 2,4-diarylpyrroles building blocks from 1,3-diaryl-4-nitro-butan-1-ones by nitro hydrolysis to a keto-aldehyde and subsequent ammonia condensation reaction has been achieved. The facile conversion of 2,4-diarylpyrroles into their alpha-nitroso analogues by their reaction with sodium nitrite generated the second building block required for the synthesis.

  DOI：

  10.1021/jo050696k
• 作为产物：
  描述：

  对乙酰氨基苯甲醛 、 苯乙酮 在 碘 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以78%的产率得到反式-N-(4-(3-氧代-3-苯基-1-丙烯基)苯基)乙酰胺
  参考文献：
  名称：

  PPh3/I2促进非碱性条件下合成查尔酮衍生物的新方法

  摘要：

  在回流温度下，在 PPh3/I2 的存在下，在 1,4-二恶烷中，通过 Claisen-Schmidt 反应合成查尔酮衍生物的简单而通用的方法已经开发出来。...

  DOI：

  10.1080/00397911.2020.1847295

文献信息

• Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans
  作者：D. Batovska、St. Parushev、A. Slavova、V. Bankova、I. Tsvetkova、M. Ninova、H. Najdenski

  DOI：10.1016/j.ejmech.2006.08.012

  日期：2007.1

  A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with the ability of compounds to interact with sulfhydryl groups. The most active were the hydroxylated chalcones as their activity related to the location

  合成了大量查耳酮，并研究了其对白色念珠菌的活性。SAR分析表明，抗真菌活性高度依赖于芳基环的取代方式，并在很大程度上与化合物与巯基相互作用的能力有关。最具活性的是羟基化查耳酮，因为它们的活性与芳基环B中酚基的位置有关，如下所示：o-OH> p-OH约为3,4-di-OH> m-OH。获得的这些相关性和其他相关性极大地有助于设计抗候选查耳酮。
• Synthesis and Evaluation of Chalcone and its Derivatives as Potential Anticholinergic Agents
  作者：Shahzad Murtaza、Khoula Zubair Mir、Adina Tatheer、Raja Summe Ullah

  DOI：10.2174/1570180815666180523085436

  日期：2019.1.15

  intention for the analysis of such compounds. This study involved the synthesis of chalcones and their pyrazoline derivatives and their screening as cholinesterase inhibitors. The newly synthesized compounds were also investigated for their antioxidant potential. Methods: Chalcones were synthesized by well-established methods of synthesis and their structural elucidation was carried out by H-NMR, 13C-NMR

  背景：查耳酮和吡唑啉的结构相似性使我们有意分析此类化合物。这项研究涉及查耳酮及其吡唑啉衍生物的合成及其作为胆碱酯酶抑制剂的筛选。还对新合成的化合物的抗氧化潜力进行了研究。 方法：采用已有的合成方法合成了con，并通过1 H-NMR，13 C-NMR，质谱和FTIR对其结构进行了阐明。为了测定合成化合物的抑制能力，采用了分光光度法，而采用DPPH自由基清除法来检测其抗氧化能力。 结果：合成了查耳酮及其吡唑啉衍生物，并通过1HNMR，13C-NMR，质谱和FTIR对其进行了表征。筛选化合物的抗阿尔茨海默氏活性，这表明化合物1g，1c和1h，1g分别显示出对乙酰胆碱酯酶和丁酰胆碱酯酶的强抑制力。采用DPPH自由基清除方法检测合成化合物的抗氧化能力，结果发现在所有合成化合物中，只有化合物1c和1b具有较强的清除能力。 结论：合成了查尔酮及其吡唑啉衍生物，并筛选了其抗阿尔茨海默氏症和抗氧化能力。将抗
• Methanol as a hydrogen source: room-temperature highly-selective transfer hydrogenation of α,β-unsaturated ketones
  作者：Nidhi Garg、Hari Prasaad Somasundharam、Pardeep Dahiya、Basker Sundararaju

  DOI：10.1039/d2cc03597a

  日期：——

  The described system offers an ideal, user-friendly protocol for the chemoselective homogeneous hydrogenation of α,β-unsaturated ketones at room temperature using methanol as a liquid organic hydrogen carrier. Excellent yields were achieved with an in situ-prepared phosphine-free Cp*Ir(III)/bipyridonate complex. Chemoselective reduction with other reducible functionalities and late-stage functionalization

  所描述的系统为使用甲醇作为液态有机氢载体在室温下对α、β-不饱和酮进行化学选择性均相氢化提供了一种理想的、用户友好的协议。使用原位制备的无膦Cp*Ir( III )/联吡啶络合物获得了优异的产率。还探索了具有其他可还原功能和后期功能化的化学选择性还原。
• In Situ Hypoiodite-Catalyzed Oxidative Rearrangement of Chalcones: Scope and Mechanistic Investigation
  作者：Meiqiong Zheng、Chao Huang、Jian-Zhong Yan、Shu-Li Xie、Shao-Jia Ke、Hai-Dong Xia、Ya-Nan Duan

  DOI：10.1021/acs.joc.2c02291

  日期：2023.2.3

  It is highly desirable to avoid using rare or toxic metals for oxidative reactions in the synthesis of pharmaceuticals and fine chemicals. Hypervalent iodine compounds are environmentally benign alternatives, but their catalytic use has been quite limited. Herein, the protocol for in situ hypoiodite-catalyzed oxidative rearrangement of chalcones is first realized under mild and metal-free conditions

  非常希望避免在药物和精细化学品的合成中使用稀有或有毒金属进行氧化反应。高价碘化合物是对环境无害的替代品，但它们的催化用途非常有限。在此，原位次碘酸盐催化查耳酮氧化重排的方案首先在温和和无金属条件下实现，为基于铊的方案提供了一种无毒、环境友好和催化的替代方案。此外，该催化方案的适用性和有效性通过克级合成和产物衍生化得到了很好的证明。更重要的是，进行了控制和核磁共振跟踪实验，以找出可能的催化物种和中间体。
• PYRIDINE DERIVATIVES
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0795545A1

  公开（公告）日：1997-09-17

  A pyridine derivative represented by the following formula: , where R1 is a methyl group or a functional group represented by any one of the following formulae:         ―CONHCH2CH2N(CH3)2         ―CONHCH2CH2CH2N(CH3)2         ―COOCH2CH2N(CH3)2         ―COOCH2CH2N(CH2CH3)2         ―NHCOCH2N(CH3)2         ―NHCOCH2N(CH2CH3)2 and R2 is a hydrogen atom, an amino group or a functional group represented by any one of the following formulae:         ―CONHCH2CH2N(CH3)2         ―COOCH2CH2N(CH3)2         ―NHCOCH2N(CH3)2         ―NHCOCH2N(CH2CH3)2 or a salt thereof directly or indirectly acts on neuronal cells in vivo and is expected to show an effect on amelioration and curing of nerve disorders due to neuronal degeneration, with application as a drug for ameliorating and curing, for example, traumatic symptoms and maladies, those induced by drugs such as alcohol, antineoplastic agents, etc., inflammatory ones, metabolic ones as observed in diabetes, etc., and furthermore those due to idiopathic degeneration of peripheral nerves, and also with application as drugs for ameliorating and curing symptoms and maladies due to degeneration of central nerves, for example, Alzheimer's disease and cerebrovascular ischemia, Down syndrome, Parkinson's disease, Huntington chorea, diseases secondary to cerebral ischemia, cerebral infarction, intracerebral bleeding, head injuries, etc., amnesia, spinal neuropathy, etc.

  下式所代表的吡啶衍生物： 其中 R1 是甲基或下式中任何一种所代表的官能团： -conhch2ch2n(ch3)2 -conhch2ch2ch2n（ch3）2 -cooch2ch2n(ch3)2 -cooch2ch2n(ch2ch3)2 -NHCOCH2N(CH3)2 -NHCOCH2N（CH2CH3）2 而 R2 是氢原子、氨基或由下式中任一式代表的官能团： -conhch2ch2n(ch3)2 -cooch2ch2n(ch3)2 -NHCOCH2N（CH3）2 -NHCOCH2N（CH2CH3）2 或其盐在体内直接或间接作用于神经元细胞，并有望显示出改善和治疗因神经元变性引起的神经紊乱的效果，可用作改善和治疗创伤性症状和弊病、酒精等药物引起的症状和弊病、抗肿瘤药物等引起的症状和弊病、炎症性症状和弊病、糖尿病等引起的代谢性症状和弊病的药物、此外，还可用于改善和治疗中枢神经退化引起的症状和疾病，如阿尔茨海默病和脑血管缺血、唐氏综合症、帕金森病、亨廷顿舞蹈症、继发于脑缺血、脑梗塞、脑出血、头部损伤等的疾病、健忘症、脊髓神经病等。