3-(3,4,5-trimethoxybenzyl)-1H-indole

• 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
• 英文名称: 3-(3,4,5-trimethoxybenzyl)-1H-indole
• 英文别名: 3-[(3,4,5-trimethoxyphenyl)methyl]-1H-indole
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: UDHKDAYLPKFVHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [1-(benzenesulfonyl)indol-3-yl]-(3,4,5-trimethoxyphenyl)methanone 在 三乙基硅烷 、 氢氧化钾 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.33h， 生成 3-(3,4,5-trimethoxybenzyl)-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents

  摘要：

  Combretastatin A-4 (CSA-4), a stilbene derivative, is a potent vascular disrupting agent (VDA) with the structural requirement of a cis-configuration to maintain a molecular geometry and a correct orientation of both phenyl groups. A series of indolic analogues of CSA-4 was synthesized by means of an efficient strategy. Six compounds (20b, 25b-27b, 32b, and 35b) were identified as potent inhibitors of tubulin polymerization and also displayed cytotoxic activities on B16 melanoma cells at a nanomolar level. Both activities were well correlated with the ability to induce morphological changes of EA-hy 926 endothelial cells. In conclusion, the cis-stilbene skeleton of CSA-4 could conveniently be replaced by the 3-aroylindolic moiety, thus avoiding any isomerization leading to inactive trans compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.037

文献信息

• Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen
  作者：Giovanni Di Gregorio、Michele Mari、Francesca Bartoccini、Giovanni Piersanti

  DOI：10.1021/acs.joc.7b01603

  日期：2017.8.18

  We present the coupling of primary and secondary benzyl alcohols with indoles to form 3-benzylated indoles and H2O that is catalyzed, for the first time, by a complex of earth-abundant iron. This transformation accommodates a variety of substrates and is distinguished by its operational simplicity, sustainability, high functional-group tolerance, and amenability to gram-scale synthesis. On the basis

  我们提出伯和仲苄醇与吲哚的偶合，以形成3-苄基化的吲哚和H 2 O，这是第一次由富地球的铁的复合物催化。这种转变可容纳多种底物，并且以其操作简单，可持续性，高官能团耐受性和对克级合成的适应性而著称。根据初步的实验观察，我们建议反应通过借入氢过程进行。
• Palladium-Catalyzed, Modular Synthesis of Highly Functionalized Indoles and Tryptophans by Direct Annulation of Substituted <i>o</i>-Haloanilines and Aldehydes
  作者：Yanxing Jia、Jieping Zhu

  DOI：10.1021/jo061471s

  日期：2006.9.1

  One-pot synthesis of indoles by a palladium-catalyzed annulation of ortho-haloanilines and aldehydes has been developed. Coupling of ortho-iodoaniline with aldehyde is realized under mild ligandless conditions [Pd(OAc)2, DABCO, DMF, 85 °C], whereas X-Phos is found to be the ligand of choice for coupling reactions involving ortho-chloroanilines/ortho-bromoanilines and aldehydes. A variety of ortho-haloanilines

  已经开发了通过钯催化的邻卤代苯胺和醛的环化一锅合成吲哚的方法。在温和的无配体条件下[Pd（OAc）2，DABCO，DMF，85°C]，可以实现邻-碘苯胺与醛的偶联，而X-Phos是涉及邻-氯苯胺/邻位的偶联反应的选择配体。-溴苯胺和醛。各种具有不同电子性质的邻卤代苯胺是合适的底物，并且包括手性醛在内的醛不消旋地参与了该反应。（耦合小号）-2- Ñ，Ñ -二叔衍生自1-谷氨酸的β-丁氧基羰基-5-氧戊酸，与邻卤代苯胺可快速接近环A取代的色氨酸，产率高至优异。
• Photocatalytic Redox-Neutral Approach to Diarylmethanes
  作者：Guozhe Guo、Yong Yuan、Xiazhen Bao、Xuehui Cao、Tongzhi Sang、Jiayuan Wang、Congde Huo

  DOI：10.1021/acs.orglett.1c02523

  日期：2021.9.3

  reaction of indole-3-acetic acid NHPI esters with indoles using a Ru photosensitizer to deliver a wide range of symmetrical and unsymmetrical 3,3′-bisindolylmethane derivatives. Furthermore, the reaction is readily adapted to the preparation of a wide variety of diarylmethane derivatives.

  我们报告了吲哚-3-乙酸NHPI 酯与吲哚的可见光诱导的氧化还原-中性脱羧交叉偶联反应，使用 Ru 光敏剂来提供各种对称和不对称的 3,3'-双吲哚甲烷衍生物。此外，该反应很容易适用于制备多种二芳基甲烷衍生物。
• Cobalt-catalysed CH-alkylation of indoles with alcohols by borrowing hydrogen methodology
  作者：Bei Zhou、Zhuang Ma、Asma M. Alenad、Carsten Kreyenschulte、Stephan Bartling、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1039/d2gc00469k

  日期：——

  interesting class of heterocyclic compounds widely used in organic synthesis and medicinal chemistry. Key for this synthesis is the use of specific cobalt-nanoparticles supported on N-doped carbon, which were conveniently prepared by the pyrolysis of a templated material generated in situ by mixing cobalt-nitrate, zinc-nitrate, 2,6-diaminopyridine, and colloidal silica, and subsequent removal of silica

  报道了吲哚与醇的一般多相钴催化 CH-烷基化。利用这种直接的借氢方法，一系列取代和官能化的吲哚很容易与包括甲醇在内的苄醇、杂环醇和脂肪醇偶联，以制备 >65 个取代的吲哚，产率从良好到优异。所得产物代表了广泛用于有机合成和药物化学的一类有趣的杂环化合物。该合成的关键是使用负载在 N 掺杂碳上的特定钴纳米颗粒，这些纳米颗粒是通过混合硝酸钴、硝酸锌、2,6-二氨基吡啶和胶体二氧化硅，然后除去二氧化硅。
• HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-<i>b</i>]quinolines &amp; related natural products
  作者：Auqib Rashid、Waseem I. Lone、Preeti Dogra、Showkat Rashid、Bilal A. Bhat

  DOI：10.1039/d4ob00414k

  日期：——

  An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3-b]quinolines is reported. This protocol, executed in aqueous HFIP has broad substrate scope and is well inclined towards the ideas of sustainable chemistry. Applications of these strategies in accessing bioactive natural products like vibrindole, norcryptotakeine, neocryptolepine and indenoindolone scaffolds

  报道了吲哚的快速无金属 C-3 烷基化及其 NIS 介导的吲哚并[2,3- b ]喹啉的偏离。该协议在水性 HFIP 中执行，具有广泛的底物范围，并且非常倾向于可持续化学的理念。这些策略在获取生物活性天然产物（如 vibrindole、norcryptotakeine、neocryptolepine 和茚并吲哚酮支架）方面的应用也已得到证实。