(E)-4-(2-hydroxy-4-methoxyphenyl)but-3-en-2-one | 124946-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(2-hydroxy-4-methoxyphenyl)but-3-en-2-one
• 英文别名: 4-(2-Hydroxy-4-methoxyphenyl)but-3-en-2-one
• CAS: 124946-65-2
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: WBNXNIPUDZZFBV-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  反式肉桂醛 、 (E)-4-(2-hydroxy-4-methoxyphenyl)but-3-en-2-one 在 四氢吡咯 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以48%的产率得到
  参考文献：
  名称：

  Dually activated Michael-Michael-acetalization cascade: facile and highly diastereoselective construction of tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one polycyclic scaffold

  摘要：

  A Michael-Michael-acetalization cascade between 4-(2-hydroxyphenyl)but-3-en-2-ones and alpha,beta-unsaturated aldehydes via a novel dual activation mode promoted by pyrrolidine was successfully established. Consequently, various novel tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one derivatives were prepared in excellent diastereoselectivities and moderate to good yields. Further diverse modification of the resulting tricyclic scaffolds provided a facile pathway to achieve a variety of tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one analogs. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.014
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 丙酮 在 sodium hydroxide 作用下， 以39%的产率得到(E)-4-(2-hydroxy-4-methoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents

  摘要：

  Twenty-eight compounds related to dehydrozingerone ( 1), isoeugenol ( 3), and 2-hydroxychalcone ( 4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR ( a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 mu g/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 mu g/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 mu g/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.

  DOI：

  10.1021/np060252z

文献信息

• Asymmetric Dearomative Cascade Multiple Functionalizations of Activated <i>N</i>-Alkylpyridinium and <i>N</i>-Alkylquinolinium Salts
  作者：Xue Song、Ru-Jie Yan、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.orglett.0c02828

  日期：2020.10.2

  An enantioselective cascade reaction of N-alkylpyridinium and -quinolinium salts with o-hydroxybenzylideneacetones to access fused polyheterocycles through cross dienamine-mediated addition followed by trapping of the dearomatized enamine-type intermediates and aminal formation has been developed. A cascade assembly of N-benzyl-4-methylpyridinium salt and cyclic 2,4-dienones is further disclosed to

  已开发出N-烷基吡啶鎓盐和-喹啉鎓盐与邻羟基苄叉基丙酮的对映选择性级联反应，通过交叉二烯胺介导的加成反应，然后捕获脱芳族化的烯胺型中间体和缩醛形成，从而进入稠合多杂环。还公开了N-苄基-4-甲基吡啶盐和环状2，4-二壬烯的级联组装，以通过重复的脱芳香化作用和芳构化活化作用给出桥连的骨架。
• Direct access to functionalized 4-nitromethyl-chromenes via a domino reaction under catalyst-free conditions
  作者：Wengang Xu、Qingcui Li、Wangwang Wang、Hua Zheng、Fanglin Zhang、Yunxing Hu

  DOI：10.1039/c5ra11333d

  日期：——

  A simple and practical tandem reaction has been established to synthesize functionalized 4-(nitromethyl)-4H-chromenes. Most products were obtained in medium to good yields. Further, chromeno[4,3-b]chromene, an important structure, was easily obtained via this strategy.

  已建立一种简单实用的串联反应，用于合成官能化的4-(硝基甲基)-4H-咔啉。大多数产物的产率在中等到良好之间。此外，具有重要结构的咔啉[4,3-b]咔啉可以通过这种策略轻松获得。
• Heilbron; Whitworth, Journal of the Chemical Society, 1923, vol. 123, p. 244
  作者：Heilbron、Whitworth

  DOI：——

  日期：——
• CCV.—The isomerism of the styryl alkyl ketones. Part III. Methoxy-2- and 4-hydroxystyryl alkyl ketones
  作者：Alexander McGookin、Donald James Sinclair

  DOI：10.1039/jr9262901578

  日期：——
• Anti-tumor agents 255: Novel glycyrrhetinic acid–dehydrozingerone conjugates as cytotoxic agents
  作者：Jin Tatsuzaki、Masahiko Taniguchi、Kenneth F. Bastow、Kyoko Nakagawa-Goto、Susan L. Morris-Natschke、Hideji Itokawa、Kimiye Baba、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2007.06.027

  日期：2007.9

  Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or Ursolic acid UA). In an in vitro anti-cancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1 A9, and KB cells with ED50 values of 0.6, 0.8, and 0.9 mu M, respectively. Similar conjugates between DZ and OA or UA were inactive suggesting that the GA component is critical for activity. Notably, although GA-DZ conjugates showed potent cytotoxic activity, the individual components (GA and DZ analogs) were inactive. Thus, GA-DZ conjugates are new chemical entities and represent interesting hits for anti-cancer drug discovery and development. (c) 2007 Elsevier Ltd. All rights reserved.