4-(2,4,5-trimethoxyphenyl)but-3-en-2-one | 14894-67-8

• 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: 4-(2,4,5-trimethoxyphenyl)but-3-en-2-one
• CAS: 14894-67-8
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: RVJHEDDPVRNHMB-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  394.2±37.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,4,5-trimethoxyphenyl)but-3-en-2-one 、 苯肼,盐酸盐 在 氧气 、 sodium acetate 、 oxovanadium(IV) sulfate 作用下， 以 水 、 甲苯 为溶剂， 反应 18.0h， 以73%的产率得到3-methyl-1-phenyl-5-(2,4,5-trimethoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis of Functionalized Pyrazoles via Vanadium-Catalyzed C–N Dehydrogenative Cross-Coupling and Fluorescence Switch-On Sensing of BSA Protein

  摘要：

  Vanadium-catalyzed C-N dehydrogenative cross-coupling of alkenyl hydrazones leading to functionalized pyrazoles is described in a 1:1 mixture of toluene/H2O using air as the terminal oxidant. Significant practical features include use of the commercial nontoxic VOSO4 as a recyclable catalyst, mild reaction conditions, scalability, and the broad substrate scope. Some of the product pyrazoles exhibit interesting photophysical properties. Fluorescence light-up sensing of BSA protein by one of the pyrazoles is also highlighted.

  DOI：

  10.1021/acs.orglett.5b02669
• 作为产物：
  描述：

  1,2,4-三甲氧基-5-丙烯基苯 在 sodium periodate 、 四氧化锇 、 1-丁基磺酸-3-甲基咪唑硫酸氢盐 、 苄基三乙基氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-(2,4,5-trimethoxyphenyl)but-3-en-2-one
  参考文献：
  名称：

  Chalcones as promising pesticidal agents against diamondback moth (Plutella xylostella): microwave-assisted synthesis and structure–activity relationship

  摘要：

  A series of chalcones (A-CH=CH-CO-B) were synthesized under microwave irradiation, and for the first time their pesticidal activity against diamondback moth (Plutella xylostella) was evaluated to identify the promising lead structures. The structure-activity relationship (SAR) analysis revealed that electron-withdrawing substituents on ring A of chalcone provided good pesticidal agents, whereas, ring B can bear either electron-withdrawing or electron-releasing substituents. Moreover, compound 22 having para-Cl substitution on ring A as well on ring B showed maximum activity with LC50 value of 170.24 mu g mL(-1).

  DOI：

  10.1007/s00044-011-9602-8

文献信息

• Reinvestigation of structure–activity relationship of methoxylated chalcones as antimalarials: Synthesis and evaluation of 2,4,5-trimethoxy substituted patterns as lead candidates derived from abundantly available natural β-asarone
  作者：Rakesh Kumar、Dinesh Mohanakrishnan、Abhishek Sharma、Naveen Kumar Kaushik、Kalpana Kalia、Arun Kumar Sinha、Dinkar Sahal

  DOI：10.1016/j.ejmech.2010.08.049

  日期：2010.11

  causes a decrease. In particular, 2,4,5-trimethoxy substitution pattern at ring A provided potent analogues which were easily derived from abundantly available natural β-asarone rich Acorus calamus oil. Cytotoxic evaluation indicated that the most active compounds 27 (IC50: 1.8 μM) and 26 (IC50: 2 μM) were also relatively non-toxic. Furthermore, compound 12 showed excellent resistance index of 1.1 against

  我们已经使用基于荧光的SYBR Green分析方法检测了一系列甲氧基化查耳酮（A –CH CH–CO– B）对恶性疟原虫（3D7株）的抗疟结构与活性的关系。我们的研究表明，环A上的释放电子的甲氧基和环B上的吸电子基团提高了抗疟药的效力，而这些基团的位置互换导致其降低。特别地，在环2,4,5-三甲氧基取代模式甲提供一种很容易从可大量获得的天然衍生的强效的类似物β细辛醚丰富菖蒲油。细胞毒性评估表明，活性最高的化合物27（IC 50：1.8μM）和26（IC 50：2μM）也是相对无毒的。此外，化合物12对P的耐氯喹Dd2菌株显示出优异的抗性指数1.1 。恶性肿瘤。
• First synthesis and absolute configuration of a β-farnesene-trimethoxystyrene conjugate isolated from Pachypodanthium confine
  作者：Masatsugu Koso、Takuya Tashiro、Mitsuru Sasaki、Hirosato Takikawa

  DOI：10.1016/j.tet.2009.09.039

  日期：2009.11

  (E)-1-[3'-(4 '',8 ''-Dimethylnona-3 '',7 ''-dienyl)cyclohex-3'-enyl]-2,4,5-trimethoxybenzene (1), a beta-farnesene-trimethoxystyrene conjugate, was isolated from Pachypodanthium confine. Its first synthesis was accomplished, and absolute configuration was determined to be R. (C) 2009 Elsevier Ltd. All rights reserved.

  (E)-1-[3'-(4,8-二甲基-3',7'-二烯-9-yl) cyclohex-3'-en-3-yl]-2,4,5-三甲氧基苯 (1)，是从 Pachypodanthium confine 中分离得到的一种化合物。它的第一种合成了成功实现，并确定了绝对构型为 R。 (C) 2009 Elsevier Ltd. 全部权利保留。