(4-bromophenyl)(1H-indol-3-yl)methanone | 1097119-36-2

• 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: (4-bromophenyl)(1H-indol-3-yl)methanone
• 英文别名: 3-(4-bromobenzoyl)-1H-indole；(4-bromophenyl)-(1H-indol-3-yl)methanone
• CAS: 1097119-36-2
• 化学式: C₁₅H₁₀BrNO
• mdl: MFCD11545383
• 分子量: 300.154
• InChiKey: NOHMBINTTHCYSF-UHFFFAOYSA-N

物化性质

• 沸点：
  468.6±20.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

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：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚 、 2-(4-溴苯基)-2-氧代乙酸 在 copper(II) acetate monohydrate 、 silver carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(4-bromophenyl)(1H-indol-3-yl)methanone
  参考文献：
  名称：

  Copper-catalyzed decarboxylative C3-acylation of free (N–H) indoles with α-oxocarboxylic acids

  摘要：

  开发了一种高效的Cu催化的自由（N-H）吲哚的脱羧C3-酰基化反应，使用α-氧代羧酸作为酰化试剂。该方法与多种官能团兼容，并提供了一种有吸引力的替代途径，可在中等至高产率下获得3-酰基吲哚。

  DOI：

  10.1039/c3ob42171f

文献信息

• Synthesis of 3-acylindoles <i>via</i> copper-mediated oxidative decarbethoxylation of ethyl arylacetates
  作者：Anjali Jaiswal、Anup Kumar Sharma、Krishna Nand Singh

  DOI：10.1039/c9ob02550b

  日期：——

  An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.

  通过在DMSO中使用Cu（OAc）2和KOtBu对易得的芳基乙酸乙酯进行氧化脱碳乙氧基化，已经实现了游离吲哚（NH）的有效区域选择性C-3酰化。
• Decarboxylative/decarbonylative C3-acylation of indoles via photocatalysis: a simple and efficient route to 3-acylindoles
  作者：Qing Shi、Pinhua Li、Xianjin Zhu、Lei Wang

  DOI：10.1039/c6gc00516k

  日期：——

  A simple and efficient strategy for the preparation of 3-acylindoles via visible-light promoted C3-acylation of free (NH)- and N-substituted indoles with a-oxocarboxylic acids was developed. The reaction tolerates a wide...

  开发了一种简单有效的策略，通过可见光促进游离（NH）-和N-取代的吲哚与α-氧代羧酸的C3-酰化反应来制备3-酰基。该反应可耐受多种...
• A novel microwave-irradiated solvent-free 3-acylation of indoles on alumina
  作者：Qiu Yu Lai、Rong Su Liao、Shao Yong Wu、Jia Xin Zhang、Xin Hong Duan

  DOI：10.1039/c3nj00854a

  日期：——

  A simple and efficient 3-acylation of indoles under microwave-heated and solvent-free conditions is developed. This general procedure uses neutral Al2O3 as a new, green and reusable catalyst giving good to high yields within short reaction times. Utilizing such an environmentally-benign methodology, a variety of indoles bearing electron-releasing or electron-withdrawing groups were conveniently acylated.

  开发出一种简单高效的3-位吲哚酰化反应方法，该方法在无溶剂条件下采用微波加热，使用中性Al2O3作为新型、绿色且可重复使用的催化剂，在短时间内获得良好至高产率的产物。运用这种环保的方法，多种带有供电子或吸电子基团的吲哚化合物得以方便地进行酰化反应。
• Temperature-Dependent Product Selectivity in the VilsmeierHaack Reaction on Bis(phenylhydrazones) of Bis(aroylmethyl) Sulfides (=1,1′-[Thiobis(methylene)]bis[arylmethanone] Bis(2-phenylhydrazones)): Synthesis of 3-Aroylindoles (=Aryl(1H-indol-3-yl)methan
  作者：Nidhin Paul、Shanmugam Muthusubramanian

  DOI：10.1002/hlca.201200198

  日期：2013.3

  The bis(phenylhydrazone) of substituted diphenacyl sulfides (=1,1′‐[thiobis(methylene)]bis[arylmethanone] bis(2‐phenylhydrazones)) 1 underwent a tandem sequence of reactions upon treatment with Vilsmeier reagent, ultimately yielding 3‐aroylindoles (=aryl(1H‐indol‐3‐yl)methanones) 3 (Scheme 1 and Table 1). The reaction seems to be product selective depending upon the reaction temperature.

  取代的苯甲酰硫的双（苯phenyl）（= 1,1'-[硫代双（亚甲基）]双[芳基甲酮]双（2-苯基hydr唑酮））1经过Vilsmeier试剂处理后串联反应，最终产生3-芳基吲哚（=芳基（1 H-吲哚-3-基）亚甲基）3（方案1和表1）。反应似乎是产物选择性的，这取决于反应温度。
• Interfacial Ti−S Bond Modulated S‐Scheme MOF/Covalent Triazine Framework Nanosheet Heterojunctions for Photocatalytic C−H Functionalization
  作者：Zhu Gao、Yi Jian、Song Yang、Qiujian Xie、Charles Joseph Ross Mcfadzean、Baosheng Wei、Juntao Tang、Jiayin Yuan、Chunyue Pan、Guipeng Yu

  DOI：10.1002/anie.202304173

  日期：2023.7.3

  Constructing photocatalyst systems to functionalize the inert C−H bonds has attracted extensive research interest. However, purposeful modulation of interfacial charge transfer in heterostructures remains a challenge, as it usually suffers from sluggish kinetics. Reported herein is an easy strategy to construct the heteroatom‐induced interface for developing the titanium‐organic frameworks (MOF‐902) @ thiophene‐based covalent triazine frameworks (CTF‐Th) nanosheets S‐scheme heterojunctions with controllable oxygen vacancies (OVs). Specifically, Ti atoms were first anchored onto the heteroatom site of CTF‐Th nanosheets, and then grown into MOF‐902 via an interfacial Ti−S linkage, generating OVs. Using in situ X‐ray photoelectron spectroscopy (XPS), extended X‐ray absorption fine structure (EXAFS) spectroscopy and density functional theory (DFT) calculations, the enhanced interfacial charge separation and transfer induced by moderate OVs in the pre‐designed S‐scheme nanosheets was validated. The heterostructures exhibited an improved efficiency in photocatalytic C3‐acylation of indoles under mild conditions with a yield 8.2 times larger than pristine CTF‐Th or MOF‐902 and enabled an extended scope of substrates (15 examples). This performance is superior to state‐of‐the‐art photocatalyst and can be retained, without significant loss, after 12 consecutive cycles.

  摘要构建光催化剂系统，使惰性 C-H 键功能化，已引起广泛的研究兴趣。然而，有目的地调节异质结构中的界面电荷转移仍然是一项挑战，因为它通常存在动力学缓慢的问题。本文报告了一种构建杂原子诱导界面的简易策略，用于开发具有可控氧空位（OV）的钛有机框架（MOF-902）@噻吩基共价三嗪框架（CTF-Th）纳米片 S 型杂结。具体来说，首先将钛原子锚定在 CTF-Th 纳米片的杂原子位点上，然后通过界面钛-S 连接长入 MOF-902，从而产生氧空位。利用原位 X 射线光电子能谱 (XPS)、扩展 X 射线吸收精细结构 (EXAFS) 光谱和密度泛函理论 (DFT) 计算，验证了预先设计的 S 型纳米片中适度的 OV 所诱导的界面电荷分离和转移的增强。这种异质结构在温和条件下光催化吲哚的 C3-酰化过程中表现出更高的效率，其产率是原始 CTF-Th 或 MOF-902 的 8.2 倍，并扩大了基质范围（15 个实例）。这种性能优于最先进的光催化剂，而且在连续 12 次循环后仍能保持，没有明显的损失。