3,3'-(octane-1,1-diyl)bis(5-bromo-1H-indole) | 1437619-24-3

• 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'-(octane-1,1-diyl)bis(5-bromo-1H-indole)
• 英文别名: 5-bromo-3-[1-(5-bromo-1H-indol-3-yl)octyl]-1H-indole
• CAS: 1437619-24-3
• 化学式: C₂₄H₂₆Br₂N₂
• 分子量: 502.292
• InChiKey: GVERUYZUNSDJHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 正辛醛 在 Fe/Al pillared clay-425°C 作用下， 以 neat (no solvent) 为溶剂， 以86%的产率得到3,3'-(octane-1,1-diyl)bis(5-bromo-1H-indole)
  参考文献：
  名称：

  Fe/Al pillared clay catalyzed solvent-free synthesis of bisindolylmethanes using diversely substituted indoles and carbonyl compounds

  摘要：

  我们开发了一种快速、无溶剂的固体酸介导合成双吲哚甲烷的方法。该工艺适用于多种具有不同保护基团存活特性的底物。铁/铝柱状粘土可重复使用 5 次以上而不会明显丧失催化活性，这也是该反应的一大特点。

  DOI：

  10.1039/c2ra22258b

文献信息

• Ruthenium Pincer Complex Catalyzed Selective Synthesis of C‐3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols
  作者：Nandita Biswas、Rahul Sharma、Dipankar Srimani

  DOI：10.1002/adsc.202000326

  日期：2020.7.29

  catalyst for C‐3 alkylation of 1H‐indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C‐3 alkylated indoles directly from 2‐(2‐nitrophenyl)ethan‐1‐ol

  在此，我们介绍了Ru-SNS配合物，该配合物可作为1H-吲哚与各种脂族伯醇和仲醇（包括环状醇以及苄醇）的C-3烷基化的有用催化剂。仅通过改变反应参数，就可以从同一组吲哚和醇中选择性地合成双吲哚基甲烷衍生物。此外，据报道，直接由2-（2-硝基苯基）乙-1-醇和Ru-络合物通过“借用氢”策略催化的醇可持续合成C-3烷基化的吲哚。该协议提供了一种原子经济的可持续途径，可用于访问结构上重要的化合物，如金刚烷，颤敏A和色胺基衍生物。
• Seralite SRC-120 resin catalyzed synthesis of bis(indolyl)methanes using indoles and low/high boiling point carbonyl compounds under solvent free conditions
  作者：Harish K. Indurthi、Reena Virdi、Papita Koli、Desaboini Nageswara Rao、Deepak K Sharma

  DOI：10.1080/00397911.2020.1849724

  日期：2021.1.2

  Abstract A highly inexpensive, and operationally simple seralite SRC-120 (strongly acidic cation exchange resin) catalyzed synthesis of 3,3′-bis(indolyl)methanes (BIMs) from indoles and low/high boiling point carbonyl compounds under solvent-free condition is reported. Synthesis of BIMs with low boiling point carbonyls at room temperature takes prolonged reaction time and give low yields at high temperature

  摘要 在无溶剂条件下，由吲哚和低/高沸点羰基化合物合成的3,3'-双（吲哚基）甲烷（BIM）的合成反应非常便宜，并且操作简单，是一种Seralite SRC-120（强酸性阳离子交换树脂）。报告。在室温下合成具有低沸点羰基的BIM会延长反应时间，并且在高温下产率较低。报道的方法克服了这些限制，并且在微波辐射条件下以较短/较短的反应时间（5-10分钟）与低/高沸点醛/酮一起使用时效果显着，并提供中等至极好的收率（65-94％）。而且，催化剂至少可循环使用五次而活性没有明显损失，这使整个过程具有吸引力且绿色环保。
• K₂S₂O₈-glucose mediated oxidative coupling of alcohols with indoles for synthesis of bis(indolyl)methanes in water
  作者：Harish K. Indurthi、Samarpita Das、Amita Kumari、Deepak K Sharma

  DOI：10.1039/d2nj02525f

  日期：——

  in water at room temperature for synthesis of bis(indolyl)methanes (BIMs) from simple indoles and alcohols is reported. The key step involves the conversion of alcohols to their corresponding carbonyl compounds and subsequent condensation with indoles from in situ generated radicals. Also, the challenging aliphatic alcohols showed good performance in the synthesis of BIMs. We also carried out a detailed

  报道了在室温下使用廉价的 K 2 S 2 O 8在水中从简单的吲哚和醇合成双（吲哚基）甲烷（BIM）。关键步骤涉及将醇转化为其相应的羰基化合物，然后与原位产生的自由基中的吲哚缩合。此外，具有挑战性的脂肪醇在 BIM 的合成中表现出良好的性能。我们还对机制进行了详细的探索。
• Natural Products for Biocides Discovery: Discovery of Arundine and It’s Derivatives as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents
  作者：Ziwen Wang、Qingmin Wang、Ancai Liao、Shengli Jin

  DOI：10.3987/com-19-14192

  日期：——

  Plant diseases are one of the natural disasters that seriously harm agricultural production, and it is very difficult to control. The discovery of new antiviral and antifungal lead compounds becomes more and more important. Natural product arundine was found to have anti-tobacco mosaic virus (TMV) activity and anti-phytopathogenic-fungus activity for the first time. A series of arundine analogues were designed, synthesized and evaluated for their antiviral and fungicidal activities. Compound 6 with excellent antiviral activity emerged as novel antiviral lead compound. Compound 7 with 12.6-38.3 mu g/mL EC50 values against 14 plant pathogens emerged as novel antifungal lead compound. This work laid a foundation for promoting the application of arundine analogues in plant protection.
• A new class of bactericidal agents against S. aureus, MRSA and VRE derived from bisindolylmethane
  作者：Deepak K. Sharma、Anil K. Tripathi、Rashmi Sharma、Reena Chib、Reyaz ur Rasool、Altaf Hussain、Baldev Singh、Anindya Goswami、Inshad A. Khan、Debaraj Mukherjee

  DOI：10.1007/s00044-013-0764-4

  日期：2014.4

  A series of bisindolylmethanes (BIMs) (1a-7j) including hybrid BIMs 6a-6c were prepared for bioevaluation. The results of initial antimicrobial screening of compounds 1a-6c showed compounds 2b, 2m, 4a and 5b to be the most potent inhibitors, exhibiting MIC as well as MBC values equal to or less than that of ciprofloxacin (0.5-2 mu g/mL) against Staphylococcus aureus, MRSA and VRE. Compound 2m was selected further to study the effect of N,N' disubstitution towards antibacterial and antitumor activity. It was observed that substitution at N,N' position (7a-7j) of 2m diminishes its antibacterial activity though in vitro antitumour activity against a panel of prostate, cervical and lung cancer cell lines remains more or less intact.