3,3'-(ethane-1,1-diyl)bis(5-methoxy-1H-indole) | 1314695-23-2

• 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'-(ethane-1,1-diyl)bis(5-methoxy-1H-indole)
• 英文别名: 5-methoxy-3-[1-(5-methoxy-1H-indol-3-yl)ethyl]-1H-indole
• CAS: 1314695-23-2
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: GNXCMOQKJGUDTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 乙醛 在 graphene oxide decorated CuBr nanoparticle 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以75%的产率得到3,3'-(ethane-1,1-diyl)bis(5-methoxy-1H-indole)
  参考文献：
  名称：

  Graphene oxide decorated with Cu(i)Br nanoparticles: a reusable catalyst for the synthesis of potent bis(indolyl)methane based anti HIV drugs

  摘要：

  一个包含在氧化石墨烯上装饰的Cu(I)Br的可重复使用的纳米催化系统已经制备，并成功应用于高效合成双(吲哚基)甲烷。合成的化合物3d显示出显著的抗HIV-1活性。

  DOI：

  10.1039/c6ra02458k

文献信息

• Palladium catalyzed alkylation of indole via aliphatic C–H bond activation of tertiary amine
  作者：K. Ramachandiran、D. Muralidharan、P.T. Perumal

  DOI：10.1016/j.tetlet.2011.04.110

  日期：2011.7

  Alkylation of indoles has been achieved via Pd-catalyzed aliphatic C–H bond activation of tertiary amine coupling with indole followed by C–N bond cleavage and subsequent addition of indole. This method involves the migration of alkane chain from tertiary amine to indole.

  吲哚的烷基化是通过Pd催化叔胺与吲哚偶联的脂肪族C–H键活化，再与吲哚偶联，然后进行C–N键裂解，然后再添加吲哚。该方法涉及烷烃链从叔胺迁移到吲哚。
• Synthesis of Bis(indolyl)methanes through an Alkylation Reaction of Indoles with Sodium Alkoxides
  作者：Bingwei Zhou、Xue Chen、Yunkui Liu、Hongwei Jin

  DOI：10.1055/a-1668-9910

  日期：2022.3

  We describe an alkylation reaction of indoles with sodium alkoxides for the synthesis of bis(indolyl)methanes. 1-Tetralone proved to be an efficient hydrogen acceptor, thus avoiding the use of precious transition metals such as Ru and Ir. This reaction features transition-metal-free conditions, uses readily available starting materials, and can be conducted on a gram scale.

  我们描述了用于合成双（吲哚基）甲烷的吲哚与醇钠的烷基化反应。1-四氢萘酮被证明是一种有效的氢受体，因此避免了使用贵的过渡金属，如 Ru 和 Ir。该反应的特点是无过渡金属条件，使用容易获得的起始材料，并且可以以克规模进行。
• Regioselective C₃Alkylation of Indoles for the Synthesis of Bis(indolyl)methanes and 3-Styryl Indoles
  作者：Ruiqin Zhang、Renchao Ma、Rener Chen、Lei Wang、Yongmin Ma

  DOI：10.1021/acs.joc.3c02551

  日期：2024.2.2

  Herein, we describe an efficient transition-metal-free regioselective C3alkylation of indoles for the synthesis of bis(indolyl)methanes and 3-styryl indoles. Nitrobenzene is employed as the oxidant to oxidize the alcohols in the presence of a strong base and the reaction avoids the use of transition metals such as Ru and Mn. The protocol provides a favorable route to access biologically active compounds

  在此，我们描述了一种有效的、无过渡金属的吲哚区域选择性C 3烷基化反应，用于合成双(吲哚基)甲烷和3-苯乙烯基吲哚。采用硝基苯作为氧化剂，在强碱存在下氧化醇，该反应避免了过渡金属如Ru和Mn的使用。该方案提供了获取生物活性化合物（如芦丁、vibrindole A 和涡轮霉素 B）的有利途径。
• Utilization of methanol and ethanol for 3,3′-bis(indolyl)methane synthesis through activation of peroxymonosulfate over a copper catalyst
  作者：Arpita Devi、Mrinmoy Manash Bharali、Subir Biswas、Tonmoy J. Bora、Jayanta K. Nath、Seonghwan Lee、Young-Bin Park、Lakshi Saikia、Manash J. Baruah、Kusum K. Bania

  DOI：10.1039/d3gc00440f

  日期：——

  Copper oxide–peroxymonosulfate is reported as a green catalyst for 3,3′-bis(indolyl)methane synthesis without the use of volatile acetaldehyde or formaldehyde.

  据报道，氧化铜过氧化单硫酸盐是一种绿色催化剂，可用于合成 3,3′-双（吲哚基）甲烷，且无需使用挥发性乙醛或甲醛。
• Iron(II) Chloride–1,1′-Binaphthyl-2,2′-diamine (FeCl2–BINAM) Complex Catalyzed Domino Synthesis of Bisindolylmethanes from Indoles and Primary Alcohols
  作者：Govindasamy Sekar、Sindhura Badigenchala、Dhandapani Ganapathy、Ankita Das、Rahul Singh

  DOI：10.1055/s-0033-1340052

  日期：——

  Biologically important bisindolylmethanes are synthesized in a domino fashion by using an iron(II) chloride-(+/-)-1,1-binaphthyl-2,2-diamine [FeCl2-(+/-)-BINAM] complex as the catalyst. This method proceeds via oxidation of a primary alcohol into the corresponding aldehyde followed by nucleophilic addition of an indole in the presence of the catalyst. A reaction intermediate is synthesized separately and converted into the bisindolylmethane product under the same reaction conditions as support for the proposed mechanism.