1-乙基-5-甲氧基吲哚 | 46182-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-乙基-5-甲氧基吲哚
• 英文名称: 1-ethyl-5-methoxyindole
• 英文别名: 1-ethyl-5-methoxy-1H-indole
• CAS: 46182-32-5
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: OUJVELDZPSZKKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-乙基-5-甲氧基吲哚 在 1-butylsulfonic-3-methylimidazolium p-toluenesulfonate 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以75%的产率得到2-(2,2-bis[1-ethyl-5-methoxy-1H-indol-3-yl]ethyl)-N-ethyl-4-methoxyaniline
  参考文献：
  名称：

  布朗斯台德酸性离子液体催化的吲哚串联三聚：在无溶剂条件下合成吲哚3,3'-三聚体的有效方法

  摘要：

  我们已经观察到1-丁烷磺酸-3-甲基咪唑鎓甲苯磺酸盐[BSMIM] OTs在纯净条件下作为吲哚串联型三聚反应有机化合物合成吲哚3,3'-三聚体的作用。已经报道了使用这种开发的方案合成具有生物学重要性的各种取代的吲哚的吲哚三聚体。从对照实验和文献中，已经提出了通过在离子液体催化剂存在下生成吲哚阳离子的可能机理。催化剂已循环使用了几次。我们方法的显着优势是反应时间短，反应纯净，无需纯化即可进行色谱分离，可购得的底物，反应条件纯净且无金属。使用协议，

  DOI：

  10.1002/jhet.3914
• 作为产物：
  描述：

  N-ethyl-N-(4-methoxyphenyl)ethenesulfinamide 在 triethyloxonium fluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以71%的产率得到1-乙基-5-甲氧基吲哚
  参考文献：
  名称：

  Baudin, Jean-Bernard; Commenil, Marie-Gabrielle; Julia, Sylvestre A., Bulletin de la Societe Chimique de France, 1996, vol. 133, # 4, p. 329 - 350

  摘要：

  DOI：

文献信息

• Divergent Dehydrogenative Coupling of Indolines with Alcohols
  作者：Xue Jiang、Weijun Tang、Dong Xue、Jianliang Xiao、Chao Wang

  DOI：10.1021/acscatal.6b03667

  日期：2017.3.3

  The dehydrogenative coupling of indolines with alcohols catalyzed by an iridium complex has been achieved to afford both N- and C3-alkylated indoles selectively, by simply changing the addition time of a base additive. The iridacycle catalyst plays multiple roles in these reactions, which dehydrogenates both amines and alcohols and catalyzes the coupling reactions. Mechanistic studies reveal that a

  通过简单地改变基础添加剂的添加时间，已经实现了二氢吲哚与被铱络合物催化的醇的脱氢偶联，从而选择性地提供了N-和C3-烷基化的吲哚。iridacycle催化剂在这些反应中起多种作用，使胺和醇都脱氢并催化偶联反应。机理研究表明，借用氢-脱氢过程和脱氢-借入氢过程分别涉及N-烷基化和C3-烷基化反应。C3-烷基化反应涉及两个sp3碳中心的直接偶联。
• Solvent-controlled highly regio-selective thieno[2,3-<i>b</i>]indole formation under metal-free conditions
  作者：Penghui Ni、Bin Li、Huawen Huang、Fuhong Xiao、Guo-Jun Deng

  DOI：10.1039/c7gc02818k

  日期：——

  An efficient three-component thieno[2,3-b]indole formation has been developed under metal-free conditions. The cascade cyclization was enabled by the acid-promoted annulation of indoles, ketones and sulfur powder, which provided modular synthesis of 2-substituted and 3-substituted thieno[2,3-b]indoles with excellent regioselectivity and broad functional group tolerance. DMF solvent played an important

  在无金属条件下，开发了一种有效的三组分噻吩并[2,3-b]吲哚的形成方法。级联环化是通过吲哚，酮和硫粉的酸促进环合实现的，从而提供了具有出色的区域选择性和宽泛的官能团耐受性的2-取代和3-取代的噻吩并[2,3-b]吲哚的模块化合成方法。DMF溶剂在区域选择性控制中起着重要作用。
• Indole and 2,4-Thiazolidinedione conjugates as potential anticancer modulators
  作者：Domenica M. Corigliano、Riyaz Syed、Sebastiano Messineo、Antonio Lupia、Rahul Patel、Chittireddy Venkata Ramana Reddy、Pramod K. Dubey、Carmela Colica、Rosario Amato、Giovambattista De Sarro、Stefano Alcaro、Adisherla Indrasena、Antonio Brunetti

  DOI：10.7717/peerj.5386

  日期：——

  Thiazolidinediones (TZDs), also called glitazones, are five-membered carbon ring molecules commonly used for the management of insulin resistance and type 2 diabetes. Recently, many prospective studies have also documented the impact of these compounds as anti-proliferative agents, though several negative side effects such as hepatotoxicity, water retention and cardiac issues have been reported. In this work, we synthesized twenty-six new TZD analogues where the thiazolidinone moiety is directly connected to an N-heterocyclic ring in order to lower their toxic effects.

  By adopting a widely applicable synthetic method, twenty-six TZD derivatives were synthesized and tested for their antiproliferative activity in MTT and Wound healing assays with PC3 (prostate cancer) and MCF-7 (breast cancer) cells.

  Three compounds, out of twenty-six, significantly decreased cellular viability and migration, and these effects were even more pronounced when compared with rosiglitazone, a well-known member of the TZD class of antidiabetic agents. As revealed by Western blot analysis, part of this antiproliferative effect was supported by apoptosis studies evaluating BCL-xL and C-PARP protein expression.

  Our data highlight the promising potential of these TZD derivatives as anti-proliferative agents for the treatment of prostate and breast cancer.

  吡唑二酮类药物（TZDs），也称为格列酮，是常用于管理胰岛素抵抗和2型糖尿病的五元碳环分子。最近，许多前瞻性研究还记录了这些化合物作为抗增殖剂的影响，尽管已报告了一些负面副作用，如肝毒性、水潴留和心脏问题。在这项工作中，我们合成了二十六种新的TZD类似物，其中噻唑烷酮基团直接连接到N-杂环环，以降低其毒性作用。 通过采用一种广泛适用的合成方法，合成了二十六种TZD衍生物，并在MTT和伤口愈合实验中测试它们对PC3（前列腺癌）和MCF-7（乳腺癌）细胞的抗增殖活性。 在二十六种化合物中，有三种显著降低了细胞的存活率和迁移率，与罗格列酮（TZD类抗糖尿病药物的知名成员）相比，这些效应甚至更加显著。根据Western blot分析，部分这种抗增殖效应得到了通过评估BCL-xL和C-PARP蛋白表达的凋亡研究的支持。 我们的数据突显了这些TZD衍生物作为治疗前列腺癌和乳腺癌的抗增殖剂的潜在前景。
• Transition-Metal-Free, Brønsted Acid-Mediated Cascade Sequence in the Reaction of Propargyl Alcohols with Sulfonamido-indoles/-indolines: Highly Substituted δ- and α-Carbolines
  作者：Karuppu Selvaraj、K. C. Kumara Swamy

  DOI：10.1021/acs.joc.8b02293

  日期：2018.12.21

  Brønsted acid-mediated, transition-metal-free reaction of propargyl alcohols with sulfonamido-indoles/-indolines under mild conditions affords highly substituted δ- or α-carbolines in good to excellent yields. This protocol involves cascade reaction sequences of Friedel–Crafts alkylation/ [1,5]-hydrogen shift/electrocyclization/elimination/ [1,2]-aryl migration followed by aromatization. An unexpected

  在温和的条件下，布朗斯台德酸介导的炔丙醇与磺酰胺基吲哚/二氢吲哚的无过渡金属反应可提供高取代度的δ-或α-咔啉，产率高至优异。该协议涉及Friedel-Crafts烷基化/ [1,5]-氢转移/电环化/消除/ [1,2]-芳基迁移然后进行芳构化的级联反应序列。还发现了意想不到的区域选择性甲苯磺酰基从吲哚的2-位迁移至6-位并消除了芳烃，从而导致α-咔啉。
• Palladium catalyzed dual C–H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives
  作者：Yongcheng Wu、Xiaopeng Peng、Bingling Luo、Fuhai Wu、Bo Liu、Fenyun Song、Peng Huang、Shijun Wen

  DOI：10.1039/c4ob02170c

  日期：——

  As the tile reaction shows, an array of dibenzocarbazoles were obtained via dual C–H functionalization of indoles with cyclic diaryliodoniums in a single operation.

  正如标题反应所示，在单次操作中通过吲哚与环状二芳基碘鎓的双C-H官能化反应获得了一系列二苯并咔唑化合物。