1,4-戊二烯-3-酮,1,5-二[4-(二甲氨基)苯基]-,(1E,4E)- | 98303-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,4-戊二烯-3-酮,1,5-二[4-(二甲氨基)苯基]-,(1E,4E)-
• 英文名称: (1E,4E)-1,5-bis[4-(N,N-dimethylamino)phenyl]-1,4-pentadien-3-one
• 英文别名: (1E,4E)-1,5-bis(4-(dimethylamino)phenyl)penta-1,4-dien-3-one；1,5-bis(4-dimethylaminophenyl)-1,4-pentadien-3-one；(1E,4E)-1,5-bis[4-(dimethylamino)phenyl]penta-1,4-dien-3-one
• CAS: 98303-49-2
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: JWTSVUUPJIIXTO-KAVGSWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-戊二烯-3-酮,1,5-二[4-(二甲氨基)苯基]-,(1E,4E)- 在 Schwartz's reagent 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (3S,5S)-3,5-Bis-(4-dimethylamino-phenyl)-4-vinyl-cyclohexanone
  参考文献：
  名称：

  Novel CuBr·SMe₂Catalyzed Conjugate Addition of 3-Trimethylsilyl-1-propenylzirconocene to Divinylketones. Stereoselective Synthesis of Poly­substituted Cyclohexanones

  摘要：

  催化量的CuBr·SMe2存在下，(E)-3-三甲基硅基-1-丙烯基锆杂环戊二烯与(E,E)-二乙烯基酮在温和条件下进行共轭加成，以良好产率得到含(E)-α,β-不饱和羰基部分的(E)-烯丙基硅烷。这些化合物经TiCl4处理后可发生高度立体控制性的硅辅助分子内环化反应，生成多取代环己酮。

  DOI：

  10.1055/s-2003-37525
• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 1,4-戊二烯-3-酮,1,5-二[4-(二甲氨基)苯基]-,(1E,4E)-
  参考文献：
  名称：

  Synthesis and Structure−Affinity Relationships of Novel Dibenzylideneacetone Derivatives as Probes for β-Amyloid Plaques

  摘要：

  A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A beta(1-42) aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two F-18 fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity folr A beta(1-42) aggregates (K-i ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for beta-amyloid imaging probes.

  DOI：

  10.1021/jm101404k

文献信息

• Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin
  作者：Guang Liang、Shulin Yang、Lijuan Jiang、Yu Zhao、Lili Shao、Jian Xiao、Faqing Ye、Yueru Li、Xiaokun Li

  DOI：10.1248/cpb.56.162

  日期：——

  The synthesis of three series of curcumin analogues with mono-carbonyl is described. Their in vitro anti-bacterial activities against seven Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the aryl ring and the space structure of the linking strain were discussed. It was observed that part of the derivatives displayed significant activity when compared with curcumin and most of them exhibited activity against the ampicillin-resisted Enterobacter cloacae. Compounds A12, B09, B13, B14 and C09 show remarkable antibacterial activity in vitro. The result showed that heterocycle or long-chain substituents may enhance the activity of curcumin analogues.

  本文描述了三种单羰基姜黄素类似物的合成。对七种革兰氏阳性和革兰氏阴性细菌进行了体外抗菌活性测试，并讨论了取代基对芳环和连接张力的空间结构的影响。观察到，与姜黄素相比，部分衍生物显示出显著的活性，并且大多数衍生物对氨苄西林抵抗的阴沟肠杆菌表现出活性。化合物A12、B09、B13、B14和C09显示出显著的体外抗菌活性。结果显示，杂环或长链取代基可能增强姜黄素类似物的活性。
• Curcumin analogs with anti-tumor and anti-angiogenic properties
  申请人：——

  公开号：US20020019382A1

  公开（公告）日：2002-02-14

  The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及表现出抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的药物配方以及使用这些化合物的方法。
• New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cycloaddition reaction and their conformational structures
  作者：N. N. Pesyan、S. Noori、S. Poorhassan、E. Şahin

  DOI：10.4314/bcse.v28i3.12

  日期：——

  Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2

  芳族醛与酮的交联醇醛缩合反应，如：丙酮和环己酮可有效地形成交叉共轭的α，β-不饱和酮，且产率极高。丙酮和环己酮衍生的α，β-不饱和酮与（硫代）巴比妥酸的分子内和分子内迈克尔加成反应导致合成新型的7,11-二芳基-2,4-二氮杂螺[5.5]十一烷-1， 3,5,9-丁酮和2,4-二芳基-1'H-螺[双环[3.3.1]壬烷-3,5'-嘧啶] -2'，4'，6'，9（3'H ）-四酮，分别具有良好的收率。通过1 H NMR，13 C NMR，FT-IR，UV-Visible，质谱和X射线晶体学技术进行结构阐明。讨论了一种可能的形成机理。结构构象还由邻近质子和双子质子之间的二面角衍生的耦合常数证明。来自巴比妥酸的螺环化合物的NH质子的1 H NMR光谱显示宽的单峰，而源自硫代巴比妥酸的螺环化合物中的这些质子显示两个不同的峰。关键词：交叉羟醛缩合，迈克尔加成，[1 + 5]环加成，巴比妥酸，构象，螺环巴比妥酸盐。化学
• Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
  作者：Shoaib Muhammad、Muhammad Naveed Javed、Firdous Imran Ali、Ahmed Bari、Imran Ali Hashmi

  DOI：10.1016/j.molliq.2019.112372

  日期：2020.2

  (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs

  离子液体（ILs）自组装形成超分子聚合物簇/聚集体。IL的聚集行为影响其在有机合成中的活性。但是，IL在有机反应中的确切作用仍是未知的。因此，重要的是要理解IL的超分子聚合聚集行为。我们正在使用电喷雾电离质谱（ESI-MS）探索IL的超分子聚合聚集行为。我们已经合成了四个亲水性IL（1-4），并研究了它们的聚集行为及其对碳-碳键形成（Knoevenagel和Claisen-Schmidt缩合）催化活性的影响。在这里，我们表明IL的聚集行为取决于阳离子和阴离子的类型和性质。ESI-MS（-ve）光谱揭示了两种不同类型的聚集，即[C n A n + 1 ] -和[A 2  + H + ] -。我们发现，催化活性随[C n A n + 1 ] -超分子聚集的增加而增加。因此，在IL中获得的最高收率的产品显示出阴离子-阴离子聚集的减少[A 2  + H +] – ESI-MS中的丰度。我们预计我们
• Antibacterials and Antimycotics: Part 1: Synthesis and Activity of 2-Pyrazoline Derivatives.
  作者：Dhananjaya NAUDURI、Gopu Bala Show REDDY

  DOI：10.1248/cpb.46.1254

  日期：——

  A series of 3-styryl-1,5-diphenyl and 5-styryl-1,3-diphenyl 2-pyrazolines of different substitutions has been synthesized by condensation of substituted alpha,beta-unsaturated ketones with phenylhydrazine hydrochloride in presence of catalytic amount of concentrated HCl. Compounds in the 3-styryl series had OMe, NMe2, NO2, OH and isopropyl substituents and those in the 5-styryl series had OMe, NMe2

  在催化剂量的催化下，将取代的α，β-不饱和酮与盐酸苯肼缩合，合成了一系列不同取代度的3-苯乙烯基-1,5-二苯基和5-苯乙烯基-1,3-二苯基2-吡唑啉。浓盐酸。3-苯乙烯基系列的化合物具有OMe，NMe2，NO2，OH和异丙基取代基，而5-苯乙烯基系列的化合物具有OMe，NMe2和NOs。就几何平均最小抑制浓度（MIC）而言，3-苯乙烯基-1,5-二苯基化合物对革兰氏阳性和革兰氏阴性细菌的抗菌活性几乎没有变化。发现4'，4“ -NMe2、4'，4” -NO2和4'，4“ -OMe化合物具有最高的活性。5-styryl-1,3-diphenyl系列的活性较低。比三苯乙烯系列。

表征谱图