4-(4'-methoxy-2',3',6'-trimethylphenyl)-but-3-ene-2-one | 54757-47-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 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-(4'-methoxy-2',3',6'-trimethylphenyl)-but-3-ene-2-one
• 英文别名: 4-(2,3,6-trimethyl-4-methoxyphenyl)-3-butene-2-one；4-(4-methoxy-2,3,6-trimethylphenyl)but-3-en-2-one；4-(4-Methoxy-2,3,6-trimethylphenyl)-3-buten-2-one
• CAS: 54757-47-0
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: NMRRLIHKRCVLLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  358.7±37.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

用途

4-(4-甲氧基-2,3,6-三甲基苯基)-3E-丁烯-2-酮是一种酮类衍生物，可作为医药中间体使用。

反应信息

• 作为反应物：
  描述：

  4-(4'-methoxy-2',3',6'-trimethylphenyl)-but-3-ene-2-one 在 sodium carbonate 、 4-甲基-2-戊酮 、 lithium chloride 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 阿维A酸
  参考文献：
  名称：

  [EN] PROCESS FOR PREPARATION OF ACITRETIN
  [FR] PROCÉDÉ DE PRÉPARATION D'ACITRÉTINE

  摘要：

  本发明提供了一种制备{(2E,4E,6E,8E)-9-(4-甲氧基-2,3,6- 三甲基)苯基-3,7-二甲基-壬二烯酸酯，即式（VI）的乙酸类似物的过程，其反应物为式（V）的3-甲酰基-巴比妥酸酯，基本无杂质，与式（IV）的5-(4-甲氧基-2,3,6-三甲基苯基)-3-甲基-戊二烯-1-三苯基磷溴化铵反应，并分离产物（VI）的化合物，用碘处理滤液以异构化不需要的顺式中间体，最终获得乙酸类似物（I），其所需的顺式异构体≥97%。

  公开号：

  WO2016042573A1
• 作为产物：
  描述：

  2,3,5-三甲基苯酚 在 四氯化锡 作用下， 生成 4-(4'-methoxy-2',3',6'-trimethylphenyl)-but-3-ene-2-one
  参考文献：
  名称：

  摘要：

  Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis, 13-cis-12-hydroxymethylretinoic acid, delta-lactone (1) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The delta-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an antihyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.

  DOI：

  10.1023/a:1016250129246

文献信息

• One-Pot Synthesis of Pyrimidinothiazolidinones and Their Anti-Inflammatory and Antimicrobial Studies
  作者：B. Lingappa、K. V. Sujith、Adithya Adhikari、N. Satheesha Rai、K. Vijaynarayana、Balakrishna Kalluraya

  DOI：10.1080/10426500902839384

  日期：2010.2.23

  es 5, monochloro acetic acid, and anhydrous sodium acetate with the appropriate aromatic aldehyde/5-nitro-2-thiophenediacetate in acetic acid/acetic anhydride medium. The structures of these new compounds were established on the basis of their analytical and spectral data. Some of the newly synthesized compounds were screened for their anti-inflammatory and antimicrobial activity. They show moderate

  在本研究中，我们报告了标题化合物 2-亚芳基-5-(2,3,6-三甲基-4-甲氧基苯基)-7-取代-5H-嘧啶基-[2,3- b]thiazolidine-3-ones 6a-j 和 2-(5-nitro-2-thienylidine)-5-(2,3,6-trimethyl-4-methoxyphenyl)-7-located-5H-pyrimidino-[2, 3-b]thiazolidine-3-ones 7a-e。因此，通过回流 4-(2,3,6-三甲基-4-甲氧基苯基)-6-甲基/芳基-3,4-二氢嘧啶-2-(1H)-以良好的收率制备了 6a-j 和 7a-e。硫酮 5、一氯乙酸和无水乙酸钠与适当的芳香醛/5-硝基-2-噻吩二乙酸盐在乙酸/乙酸酐介质中。这些新化合物的结构是根据它们的分析和光谱数据确定的。筛选了一些新合成的化合物的抗炎和抗菌活性。它们显示出中等的抗炎活性，其中一些被
• Polyene compounds useful in the treatment of psoriasis and allergic
  申请人：USV Pharmaceutical Corp.

  公开号：US04534979A1

  公开（公告）日：1985-08-13

  Polyene compounds represented by the general formulae ##STR1## in which: R and R.sub.1 are each hydrogen or an alkyl group of from 1 to 5 carbon atoms; R.sub.2 is an alkyl group of from 1 to 5 carbon atoms; R.sub.3 is hydroxyl, alkoxy of from 1 to 5 carbon atoms, NH.sub.2, NHR.sub.2 or NR.sub.2 R.sub.2 and Z is a cycloalkyl, cycloalkenyl or cycloalkdienyl group substituted with from 0 to 5 alkyl groups, a keto group or a hydroxyl group or a phenyl group substituted with from 0 to 4 hydroxy, alkoxy, alkyl, aryloxy, aralkyloxy or trifluoromethyl groups or halogen atoms or combinations thereof and the pharmaceutically-acceptable salts thereof. The foregoing compounds have been found to be effective in the treatment of psoriasis, inflammatory conditions and allergic responses.

  通式为##STR1##的聚烯烃化合物，其中：R和R.sub.1均为氢或1至5个碳原子的烷基；R.sub.2为1至5个碳原子的烷基；R.sub.3为羟基、1至5个碳原子的烷氧基、NH.sub.2、NHR.sub.2或NR.sub.2 R.sub.2；Z为环烷基、环烯基或环二烯基，取代有0至5个烷基、酮基或羟基，或取代有0至4个羟基、烷氧基、烷基、芳氧基、芳基烷氧基或三氟甲基基团或卤素原子或它们的组合，以及其药学上可接受的盐。已发现上述化合物对银屑病、炎症和过敏反应的治疗具有有效性。
• Dihydroretinoic acids and their derivatives. Synthesis and biological activity
  作者：Beverly A. Pawson、H. C. Cheung、Ru-Jen L. Han、Patrick W. Trown、Margaret Buck、Roseanne Hansen、W. Bollag、U. Ineichen、H. Pleil

  DOI：10.1021/jm00217a011

  日期：1977.7

  The syntheses of the ring and four side-chain dihydroretinoic acids and/or their esters, 3-7, are described. The syntheses of several other retinoids containing a substituted aromatic ring are also included. The biological activity of the compounds was evaluated in vivo in a chemically induced mouse skin papilloma test and in vitro in two vitamin A deficient assays. The activity observed for 1a, 1c, and 2a in the former test was partially retained in the dihydro derivatives 4b, 4c, and 6b. Similar results were found in the in vitro assays.