4-((5-bromo-1H-indol-3-yl)methyl)-N,N-dimethylaniline | 1193377-98-8

• 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: 4-((5-bromo-1H-indol-3-yl)methyl)-N,N-dimethylaniline
• 英文别名: 4-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylaniline
• CAS: 1193377-98-8
• 化学式: C₁₇H₁₇BrN₂
• 分子量: 329.239
• InChiKey: QBGVQISGNZFMSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 N,N-二甲基苯胺 在 氧气 、 孟加拉红内酯 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以45%的产率得到4-((5-bromo-1H-indol-3-yl)methyl)-N,N-dimethylaniline
  参考文献：
  名称：

  通过sp3 C-H键的氧化在可见光下促进叔胺与吲哚的烷基化

  摘要：

  首次报道了使用叔胺和吲哚合成可见光驱动的3-芳基甲基吲哚衍生物的反应。当在温和的反应条件下，将玫瑰红用作光敏剂，并将空气用作绿色氧化剂时，可获得相应的产物，收率高达70％，并且吲哚上的各种官能团均具有良好的耐受性。

  DOI：

  10.1002/adsc.201701131

文献信息

• K2S2O8-Mediated Arylmethylation of Indoles with Tertiary Amines via sp3 C–H Oxidation in Water
  作者：Lal Yadav、Rana Singh、Manjula Singh、Arvind Yadav

  DOI：10.1055/s-0037-1610264

  日期：2018.10

  has been achieved using tertiary amines as both methylene (-CH2-) transfer and arylmethylation agents and K2S2O8 as a convenient oxidant. The key feature of this protocol is the utilisation of K2S2O8 as an inexpensive and easy to handle radical surrogate that can effectively promote the reaction, leading to the formation of C(sp2)–C(sp3)–C(sp2) bonds via sp3 C–H bond oxidation in water at room temperature

  使用叔胺作为亚甲基 (-CH2-) 转移剂和芳基甲基化剂，使用 K2S2O8 作为方便的氧化剂，已经实现了无过渡金属和催化剂的 3-芳基甲基吲哚的高效合成。该协议的主要特点是利用 K2S2O8 作为一种廉价且易于处理的自由基替代物，可以有效地促进反应，从而通过 sp3 C 形成 C(sp2)–C(sp3)–C(sp2) 键-H 键在室温下以一锅法在水中氧化。
• Metal and acid-free visible light-mediated Friedel-Crafts alkylation reactions of indole with anilines
  作者：Xiao-Qiang Dai、Wen-Xiu Xu、Ya-Long Wen、Xing-Hai Liu、Jian-Quan Weng

  DOI：10.1016/j.tetlet.2018.06.046

  日期：2018.7

  Metal and acid-free visible light-induced Friedel-Crafts C3-alkylation reactions of indole derivatives were developed using N,N-dimethylanilines as the carbon source. A cheap and readily available organic dye, Rose Bengal, was applied as the photocatalyst. This environmentally friendly transformation afforded C3-alkylated indoles in moderate to good yields under mild conditions.

  以N，N-二甲基苯胺为碳源，开发了无金属和无酸的可见光诱导的吲哚衍生物的C3-烷基化反应。一种廉价且容易获得的有机染料玫瑰红被用作光催化剂。这种环境友好的转化在温和的条件下以中等至良好的收率提供了C3-烷基化的吲哚。
• A novel multi-component reaction of indole, formaldehyde, and tertiary aromatic amines
  作者：Atul Kumar、Siddharth Sharma、Ram Awatar Maurya

  DOI：10.1016/j.tetlet.2009.08.046

  日期：2009.10

  A novel multi-component reaction of indoles, formaldehydes, and tertiary aromatic amines is described for the synthesis of dialkylaminoarylated indoles using silica-supported perchloric acid (HClO4–SiO2) as an inexpensive and highly efficient catalyst. The key features of this multi-component reactions are operational simplicity, mild reaction conditions, regioselectivity, and recycling of catalyst

  描述了一种新颖的吲哚，甲醛和芳族叔胺的多组分反应，该反应使用二氧化硅负载的高氯酸（HClO 4 -SiO 2）作为廉价且高效的催化剂来合成二烷基氨基芳基化的吲哚。这种多组分反应的关键特征是操作简便，温和的反应条件，区域选择性和催化剂的循环利用。
• PMA-SiO₂–Mediated MCR in PEG-400: A Greener aza-Friedel–Crafts Reaction Leading to 3-Arylmethyl/Diarylmethyl Indoles
  作者：Dinne Naresh Kumar Reddy、Kothapalli Bannoth Chandrasekhar、Yaddanapudi Sesha Siva Ganesh、Srikanth Sharathchandra Gorantla、Siddabathuni Ramanjaneyulu、K. Shiva Kumar、Manojit Pal

  DOI：10.1080/00397911.2014.966392

  日期：2015.2.16

  A greener approach for the synthesis of 3-arylmethyl/diarylmethyl indoles has been achieved via a PMA-SiO2-mediated three-component reaction (the aza-Friedel-Crafts reaction) involving indoles, aldehydes, and N,N-disubstituted anilines in PEG-400. A variety of indole derivatives were prepared by using this operationally simple and straightforward methodology in acceptable yields.
• Corrigenda
  作者：Reddy, Dinne Naresh Kumar、Chandrasekhar, Kothapalli Bannoth、Ganesh, Yaddanapudi Sesha Siva、Gorantla, Srikanth Sharathchandra、Ramanjaneyulu, Siddabathuni、Kumar, K. Shiva、Pal, Manojit

  DOI：10.1080/00397911.2015.1087250

  日期：2015.10.18