(2E)-1-(2H-1,3-benzodioxol-5-yl)-3-(4-methylphenyl)prop-2-en-1-one | 1002925-69-0

• 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
• 英文名称: (2E)-1-(2H-1,3-benzodioxol-5-yl)-3-(4-methylphenyl)prop-2-en-1-one
• 英文别名: (2E)-1-(1,3-benzodioxol-5-yl)-3-(4-methylphenyl)-2-propen-1-one；(E)-1-(benzo[d][1,3]dioxol-5-yl)-3-p-tolylprop-2-en-1-one；(E)-1-(1,3-benzodioxol-5-yl)-3-(p-tolyl)prop-2-en-1-one；(E)-1-(1,3-benzodioxol-5-yl)-3-(4-methylphenyl)prop-2-en-1-one
• CAS: 1002925-69-0
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: MQLQQXYOTCEOBS-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2H-1,3-benzodioxol-5-yl)-3-(4-methylphenyl)prop-2-en-1-one 在 iron(III) trifluoromethanesulfonate 、 3,5-双(三氟甲基)苯硼酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到
  参考文献：
  名称：

  通过双齿二铁刘易斯酸活化策略催化未活化的芳基乙烯基酮的纳扎罗夫催化高效反应

  摘要：

  通过使用芳基硼酸/ Fe（OTf）3可以完成未活化的芳基乙烯基酮的高效催化Nazarov反应。在利用极其广泛的底物范围方面获得了重大进展，从而以高产率获得了茚满酮，并具有较高的区域选择性和非对映选择性。机理研究支持双齿二铁路易斯酸的催化，芳基乙烯基酮通过同时配位的强双亲电活化在实现高反应效率方面起着关键作用。

  DOI：

  10.1002/adsc.201700820
• 作为产物：
  描述：

  胡椒环 在 sodium hydroxide 、 zinc(II) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 (2E)-1-(2H-1,3-benzodioxol-5-yl)-3-(4-methylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and characterization of novel benzo[d][1,3]dioxole gathered pyrazole derivatives and their antimicrobial evaluation

  摘要：

  DOI：

  10.1007/s00044-014-0952-x

文献信息

• Solution phase synthesis of a spiro[pyrrolidine-2,3′-oxindole] library via a three component 1,3-dipolar cycloaddition reaction
  作者：Demosthenes Fokas、William J. Ryan、David S. Casebier、David L. Coffen

  DOI：10.1016/s0040-4039(98)00234-2

  日期：1998.4

  A combinatorial library of 26,500 spiro[pyrrolidine-2,3′-oxindoles] was prepared in a single-compound format by a facile intermolecular 1,3-dipolar cycloaddition. An azomethine ylide, generated by the decarboxylative condensation of an isatin 1 with an α-amino acid 2, was trapped by a trans-chalcone3 to afford heterocycles of the general structure 4. The regio- and stereochemistry of a representative

  通过容易的分子间1,3-偶极环加成，以单化合物形式制备了26,500个螺[吡咯烷-2,3'-羟吲哚]的组合文库。由靛红1与α-氨基酸2的脱羧缩合生成的甲亚胺叶立德被反式查尔酮3捕获，从而得到具有一般结构4的杂环。代表性产品的区域和立体化学由单晶X射线结构确定。
• Design, synthesis and biological evaluation of oxygenated chalcones as potent and selective MAO-B inhibitors
  作者：Della Grace Thomas Parambi、Jong Min Oh、Seung Cheol Baek、Jae Pil Lee、Anna Rita Tondo、Orazio Nicolotti、Hoon Kim、Bijo Mathew

  DOI：10.1016/j.bioorg.2019.103335

  日期：2019.12

  addition, most of the derivatives potently inhibited MAO-A and O6 was the most potent inhibitor with an IC50 value of 0.029 µM, followed by O3, O4, O9, and O2 (IC50 = 0.035, 0.053, 0.072, and 0.082 µM, respectively). O23 had a high selectivity index (SI) value for MAO-B of 138.1, and O20 (IC50 value for MAO-B = 0.010 µM) had an extremely high SI of >4000. In dialysis experiments, inhibitions of MAO-A and

  本研究记录了氧化查尔酮（O1-O26）衍生物的合成及其抑制单胺氧化酶的能力。检查的所有26种衍生物均显示出对MAO-B的有效抑制活性。化合物O23对MAO-B表现出最大的抑制活性，IC 50值为0.0021 µM，其次是化合物O10和O17（IC 50分别 为0.0030和0.0034 µM）。此外，大多数衍生物均能有效抑制MAO-A和O6，是最有效的抑制剂，IC 50值为0.029 µM，其次是O3，O4，O9和O3。O2（IC 50 分别为0.035、0.053、0.072和0.082 µM）。O23对MAO-B的选择性指数（SI）值为138.1，而O20（对于MAO-B的IC 50值为0.010 µM）具有非常高的SI> 4000。在透析实验中，O6和O23对MAO-A和MAO-B的抑制作用分别恢复到了各自的可逆参考水平，表明这两种都是可逆抑制剂。动力学研究表明，O6和O23分别以K
• Microwave induced synthesis of novel 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as potential antitumor agents
  作者：Braulio Insuasty、Fabián Orozco、Jairo Quiroga、Rodrigo Abonia、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.ejmech.2007.12.005

  日期：2008.9

  4-amino-8-aryl-6-(1,3-benzodioxol-5-yl)-8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazep ines 5a-f were obtained regioselectively from the reaction of 4,5,6-triaminopyrimidine 1 with 1equiv of methylenedioxychalcones 2a-f and 3a-f, under microwave irradiation. Detailed NMR measurements confirm the high regioselectivity of this reaction. These compounds have been evaluated in the US National Cancer Institute (NCI) for

  一系列新的外消旋4-氨基-6-芳基-8-（1,3-苯并二恶唑-5-基）-8,9-二氢-7H-嘧啶[4,5-b] [1,4]二氮杂in 4a-f和4-氨基-8-芳基-6-（1,3-苯并二恶唑-5-基）-8,9-二氢-7H-嘧啶基[4,5-b] [1,4]二氮杂in 5a -f是在微波辐射下由4,5,6-三氨基嘧啶1与1当量的亚甲基二氧基查耳酮2a-f和3a-f的区域选择性获得的。详细的NMR测量证实了该反应的高区域选择性。这些化合物已在美国国家癌症研究所（NCI）中评估了其抑制大约60种不同人类肿瘤细胞系的能力，其中4e，5a和5b分别对47、11和37个癌细胞系表现出显着的活性。体外测定，最重要的GI50值范围为0.068至0.35 microM。
• Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi
  作者：Deise M. Borchhardt、Alessandra Mascarello、Louise Domeneghini Chiaradia、Ricardo J. Nunes、Glaucius Oliva、Rosendo A. Yunes、Adriano D. Andricopulo

  DOI：10.1590/s0103-50532010000100021

  日期：——

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.
• Catalytic Efficient Nazarov Reaction of Unactivated Aryl Vinyl Ketones via a Bidentate Diiron Lewis Acid Activation Strategy
  作者：Xin Zhou、Yukun Zhao、Yang Cao、Lirong He

  DOI：10.1002/adsc.201700820

  日期：2017.10.4

  has been accomplished by employing aryl boric acid/Fe(OTf)3. Significant progress was obtained in utilizing an extremely broad substrate scope, giving indanones in high yields with high regioselectivities and diastereoselectivities. The mechanistic investigation supports a bidentate diiron Lewis acid catalysis, and the strong double electrophilic activation of aryl vinyl ketones via simultaneous coordination

  通过使用芳基硼酸/ Fe（OTf）3可以完成未活化的芳基乙烯基酮的高效催化Nazarov反应。在利用极其广泛的底物范围方面获得了重大进展，从而以高产率获得了茚满酮，并具有较高的区域选择性和非对映选择性。机理研究支持双齿二铁路易斯酸的催化，芳基乙烯基酮通过同时配位的强双亲电活化在实现高反应效率方面起着关键作用。