(4,7-二甲氧基-1-苯并噻吩-2-基)甲醇 | 190328-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: (4,7-二甲氧基-1-苯并噻吩-2-基)甲醇
• 英文名称: (4,7-dimethoxybenzo[b]thiophen-2-yl)methanol
• 英文别名: Benzo[b]thiophene-2-methanol, 4,7-dimethoxy-；(4,7-dimethoxy-1-benzothiophen-2-yl)methanol
• CAS: 190328-70-2
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: CBFMKYQUDWCPKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4,7-二甲氧基-1-苯并噻吩-2-基)甲醇 在 盐酸 、 硝酸 作用下， 反应 1.0h， 以48%的产率得到5,6-dichloro-2-(hydroxymethyl)benzo[b]thiophene-4,7-dione
  参考文献：
  名称：

  Synthesis and antifungal activity of 5-arylamino-4,7-dioxobenzo[b]thiophenes

  摘要：

  5-Arylamino-4,7-dioxobenzo[b]thiophenes 3-6 were synthesized and tested for in vitro antifungal activity against Candida and Aspergillus species. 5-Arylamino-6-chloro-2-(methoxycarbonyl)-4,7-dioxobenzo[b]thiophenes 5 showed, in general, more potent antifungal activity against Candida species than the other 4,7-dioxobenzo[b]thiophenes 3, 4 and 6. The results suggest that 5-arylamino-4,7-dioxobenzo[b]thiophenes would be potent antifungal agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.042
• 作为产物：
  描述：

  3,6-二甲氧基-2-硝基苯甲醛 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (4,7-二甲氧基-1-苯并噻吩-2-基)甲醇
  参考文献：
  名称：

  Synthesis and antifungal activity of 5-arylamino-4,7-dioxobenzo[b]thiophenes

  摘要：

  5-Arylamino-4,7-dioxobenzo[b]thiophenes 3-6 were synthesized and tested for in vitro antifungal activity against Candida and Aspergillus species. 5-Arylamino-6-chloro-2-(methoxycarbonyl)-4,7-dioxobenzo[b]thiophenes 5 showed, in general, more potent antifungal activity against Candida species than the other 4,7-dioxobenzo[b]thiophenes 3, 4 and 6. The results suggest that 5-arylamino-4,7-dioxobenzo[b]thiophenes would be potent antifungal agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.042

文献信息

• Studies on Quinones. Part 30. Synthesis of Benzo[<i>b</i>]thiophene-4, 7-Quinones
  作者：Jaime A. Valderrama、Claudio Valderrama

  DOI：10.1080/00397919708006822

  日期：1997.6

  Abstract The synthesis of a variety of benzo[b]thiophene-4, 7-quinones (4a-f), by oxidative demethylation of the corresponding 4, 7-dimethoxybenzo[b]thiophenes (3a-f), with cerium (IV) ammonium nitrate is reported. Heterocycles (3a, b), were prepared by cyclization of the corresponding 2, 5-dimethoxy-6-nitrobenzaldehyde (1a), and 2, 5-dimethoxy-6-nitroacetophenone (1b), with methyl thioglycolate.

  摘要 通过氧化去甲基化相应的 4, 7-二甲氧基苯并 [b] 噻吩 (3a-f) 与铈 (IV)，合成多种苯并 [b] 噻吩-4, 7-醌 (4a-f)据报道硝酸铵。杂环化合物 (3a, b) 是通过相应的 2, 5-二甲氧基-6-硝基苯甲醛 (1a) 和 2, 5-二甲氧基-6-硝基苯乙酮 (1b) 与巯基乙酸甲酯环化制备的。
• Synthesis and Antitumor Evaluation of Thiophene Analogs of Kigelinone
  作者：Jaime Valderrama、Omar Espinoza、Jaime Rodriguez、Cristina Theoduloz

  DOI：10.2174/157017809788490006

  日期：2009.6.1

  The synthesis of kigelinone thiophene analogs and related naphtho[2,3-b]thiophene-4,9-quinones from 2- substituted 4,7-dimethoxybenzo[b]thiophenes via an oxidative deprotection, Diels-Alder, and oxidative aromatization reaction sequence is reported. The 2-substituted naphtho[2,3-b]thiophene-4,9-quinones display significant antitumor activity in the range IC50 1.1-47 μM on a panel of four distinct human

  由2-取代的4,7-二甲氧基苯并[b]噻吩经氧化脱保护，Diels-Alder和氧化芳构化反应顺序合成基基利农酮噻吩类似物和相关的萘并[2,3-b]噻吩-4,9-醌被报道。2-取代的萘并[2,3-b]噻吩-4,9-醌在一组四种不同的人类癌细胞系中的IC50范围为1.1-47μM时显示出显着的抗肿瘤活性。
• Solvent-Free Microwave Synthesis of 3-(4-Benzo[b]thiophene-2-carbonyl)-1-piperazinyl-1-benzo[b]thiophen-2-yl-1-propanones. New Hetero Bis-Ligands with Potential 5-HT1A Serotonergic Activity
  作者：Hernán Pessoa-Mahana、Johann Kosche C.、Nadia Ron H.、Gonzalo Recabarren-Gajardo、Claudio Saitz B.、Ramiro Araya-Maturana、C. David Pessoa-Mahana

  DOI：10.3987/com-08-11326

  日期：——

  A novel series of 2-benzothiophenealkylpiperazine derivatives 11 (a-d) with potential affinity at 5-HT1A serotonin receptors have been synthesized via solvent-free, microwave-promoted Michael addition of benzo[b]thiophene piperazine derivatives 6(a-c) to substituted benzo[b]thiophen-2-yl propenones 10(b,c).
• Studies on Quinones. Part 38: synthesis and leishmanicidal activity of sesquiterpene 1,4-Quinones
  作者：Jaime A Valderrama、Julio Benites、Manuel Cortés、Hernán Pessoa-Mahana、Eric Prina、Alain Fournet

  DOI：10.1016/j.bmc.2003.08.011

  日期：2003.11

  The reaction of (+)-euryfuran 1 with several benzo-, naphtho- and benzo[b]thiophene-1,4-quinones in acetic acid yields the corresponding euryfuryl-1.4-quinones 3, 5, 7, 8, 10, 12, and 14. The structure of compounds 7, 8, 12, and 14 was assigned through 2D NMR H-1-C-13 HMBC experiments. The influence of the acidity of the solvent upon the reactivity and regioselectivity of the quinones to the oxidative coupling reaction, is discussed. The in vitro activity of the euryfurylquinones and their corresponding precursors against Leishmania amazonensis is described. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring
  作者：Ricardo A. Tapia、Luz Alegria、Carlos D. Pessoa、Cristian Salas、Manuel J. Cortés、Jaime A. Valderrama、Marie-Elisabeth Sarciron、Félix Pautet、Nadia Walchshofer、Houda Fillion

  DOI：10.1016/s0968-0896(03)00122-6

  日期：2003.5

  The synthesis of tetracyclic quinones 10a,b, 14a,b, 19a,b and 20a,b is described. The preparations involve regioselective Diels-Alder reactions via trapping the thiazole o-quinodimethane 9 with several benzofuranquinones and benzothiophenequinones. The structure of the regioisomers was assigned through 2D NMR H-1-C-13 HMBC experiments performed on 10a and 14a. Compounds 10a,b, 14a as well as phenol I and the starting quinones 2, 5, 7 and 15 are evaluated against Leishmania sp., Toxoplasma gondii and THP-1 cells. Almost all the tested compounds exhibit significant antiprotozoal activities with lower cytotoxicities than the reference compounds. Among them, quitiones 2 and 14a possess the best activities towards L. donovani and T. gondii with the lowest toxicities. (C) 2003 Elsevier Science Ltd. All rights reserved.