5-溴-2-(4-甲氧基苯基)-1H-吲哚 | 851530-48-8

• 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
• 中文名称: 5-溴-2-(4-甲氧基苯基)-1H-吲哚
• 英文名称: 5-bromo-2-(4-methoxyphenyl)-1H-indole
• CAS: 851530-48-8
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: DGIPPVLCMMJSRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25
• 氢给体数：
  1
• 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：

  5-溴-2-(4-甲氧基苯基)-1H-吲哚 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以13%的产率得到4-(5-bromo-1H-indol-2-yl)phenol
  参考文献：
  名称：

  Synthesis and characterization of novel phenylindoles as potential probes for imaging of β-amyloid plaques in the brain

  摘要：

  We synthesized a novel series of phenylindole (PI) derivatives and evaluated their biological activities as probes for imaging A beta plaques in vivo. The affinity for A beta plaques was assessed by an in vitro-binding assay using pre-formed synthetic A beta aggregates. 2-Phenyl-1H-indole (2-PI) derivatives showed high affinity for A beta 42 aggregates with K-i values ranging from 4 to 32 nM. 2-PI derivatives clearly stained A beta plaques in an animal model of AD. In biodistribution experiments using normal mice, 2-PI derivatives displayed sufficient uptake for imaging, ranging from 1.1% to 2.6% ID/g. Although additional modifications are necessary to improve uptake by and clearance from the brain, 2-PI derivatives may be useful as a backbone structure to develop novel Ab imaging agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.013
• 作为产物：
  描述：

  N-(4-bromo-2-(2,2-dibromovinyl)phenyl)methanesulfonamide 在 potassium phosphate 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.0h， 生成 5-溴-2-(4-甲氧基苯基)-1H-吲哚
  参考文献：
  名称：

  The facile synthesis of 2-bromoindoles via Cs₂CO₃-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions

  摘要：

  在不含过渡金属的条件下，通过 Cs2CO3 促进的 2-(偕溴乙烯基)-N-甲基磺酰基苯胺的分子内环化，可以轻松制备 2-溴吲哚，收率优异。该方法可以扩展到相应的 2-氯吲哚的合成。反应机理表明，环化是通过关键中间体苯乙炔基溴发生的，然后是一锅环化。

  DOI：

  10.1039/c2ra22172a

文献信息

• The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
  作者：Shuling Yu、Linjun Qi、Kun Hu、Julin Gong、Tianxing Cheng、Qingzong Wang、Jiuxi Chen、Huayue Wu

  DOI：10.1021/acs.joc.7b00148

  日期：2017.4.7

  A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations

  首次开发了钯催化的2-（2-氨基芳基）乙腈与芳基硼酸的串联串联加成/环化反应，实现了直接构建吲哚骨架的新策略。该系统显示出良好的官能团耐受性和出色的化学选择性。特别地，卤素（例如，溴和碘）取代基适合于进一步的合成精细化，从而扩大了产物的多样性。初步的机械实验表明，这种转化涉及相继的亲核加成，然后进行分子内环化。
• Direct C-Arylation of Free (NH)-Indoles and Pyrroles Catalyzed by Ar−Rh(III) Complexes Assembled In Situ
  作者：Xiang Wang、Benjamin S. Lane、Dalibor Sames

  DOI：10.1021/ja050279p

  日期：2005.4.1

  Ar-Rh(III) pivalate complexes assembled in situ from the reaction of [RhCl(coe)2]2 (coe = cis-cyclooctene), [p-(CF3)C6H4]3P, and CsOPiv effectively catalyzed the direct C-arylation of free (NH)-indoles and (NH)-pyrroles in good yields and with high regioselectivity. The reaction displayed excellent functional group compatibility and low moisture sensitivity. Kinetics studies support a mechanism involving

  由 [RhCl(coe)2]2（coe = 顺式环辛烯）、[p-(CF3)C6H4]3P 和 CsOPiv 的反应原位组装的 Ar-Rh(III) 新戊酸酯配合物有效地催化了直接的 C-芳基化以高产率和高区域选择性分离游离 (NH)-吲哚和 (NH)-吡咯。该反应显示出优异的官能团相容性和低湿敏性。动力学研究支持一种机制，包括配合物 2（催化剂的静止状态）中的吲哚置换膦，然后是限速 CH 键金属化。
• Pd-catalyzed C–H bond activation of Indoles for Suzuki reaction
  作者：Isita Banerjee、Keshab Ch Ghosh、Surajit Sinha

  DOI：10.1007/s12039-019-1649-y

  日期：2019.8

  practical method for Suzuki coupling by which unprotected or N-protected indoles may be selectively arylated in the C2-position through direct C–H bond activation by electrophilic \(\hbox Pd(TFA)}_2}\) catalyst. The protocol is operationally simple as it is carried out in dioxane/water mixture, and air as the sole oxidant at room temperature. Various 2-arylated indoles were obtained in good yields

  摘要我们提出了一种铃木偶联的实用方法，该方法可以通过亲电\（\ hbox Pd（TFA）} _ 2} \）通过直接的C–H键激活，将未保护或受N保护的吲哚选择性地芳基化在C2位。催化剂。该方案操作简单，因为它是在二恶烷/水的混合物中进行的，而空气是室温下的唯一氧化剂。以良好的产率获得了各种2-芳基化的吲哚。该方案也适用于苯并呋喃，吡咯和噻吩。 图形摘要在环境条件下，使用Pd（II）催化剂通过C–H活化使杂环选择性C-2芳基化。有机钯中间体的C3-C2迁移控制了反应路径。
• Microwave irradiated synthesis of 2-bromo(chloro)indoles via intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in the presence of TBAF under metal-free conditions
  作者：Min Wang、Pinhua Li、Wei Chen、Lei Wang

  DOI：10.1039/c4ra00603h

  日期：——

  2-Bromo(chloro)indoles were readily prepared through TBAF-promoted intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in excellent yields under metal-free and microwave irradiation conditions.

  2-溴（氯）吲哚可通过TBAF促进的2-（gem-二溴（氯）乙烯）苯胺的分子内环化反应，在无金属和微波辐射条件下，以极高的产率轻松制备。
• Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles
  作者：Shuling Yu、Kun Hu、Julin Gong、Linjun Qi、Jianghe Zhu、Yetong Zhang、Tianxing Cheng、Jiuxi Chen

  DOI：10.1039/c7ob00572e

  日期：——

  was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover

  通过在水性介质中钯催化的芳基三氟硼酸钾与脂肪族腈的串联/串联加成/环化反应，开发了构建2-芳基吲哚的有效方案。使用水作为反应介质使合成过程对环境无害。提出了一个合理的机制，形成2-芳基吲哚涉及亲核加成顺序，然后进行分子内环化。此外，这种催化串联转化的效用也在有效的克级合成中得到了证明。该方法提供了另一种可替代的合成工具，可用于获得更多种类的2-芳基吲哚。