(5-methyl-1H-indol-3-yl)(phenyl)methanone | 69622-38-4

• 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: (5-methyl-1H-indol-3-yl)(phenyl)methanone
• 英文别名: (5-methyl-indol-3-yl)-phenyl-methanone；(5-methyl-1H-indol-3-yl)-phenylmethanone
• CAS: 69622-38-4
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: KXYREGAZNGPEGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5-methyl-1H-indol-3-yl)(phenyl)methanone 在 亚硝酸特丁酯 、 oxone||potassium monopersulfate triple salt 、 氧气 、 palladium diacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 6.25h， 生成 (1-benzyl-5-methyl-4-nitro-1H-indol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Palladium-Catalyzed Weak-Chelation-Assisted C4-Nitration of Indoles with tert-Butyl Nitrite: Formal Access to Aminated Indoles

  摘要：

  DOI：

  10.1021/acs.orglett.3c03921
• 作为产物：
  描述：

  N-benzoyl-5-methylindole 在 aluminum oxide 作用下， 以 neat (no solvent) 为溶剂， 反应 0.07h， 以95%的产率得到(5-methyl-1H-indol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  A novel microwave-irradiated solvent-free 3-acylation of indoles on alumina

  摘要：

  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。

  DOI：

  10.1039/c3nj00854a

文献信息

• Selective C–H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis
  作者：Jitan Zhang、Manyi Wu、Jian Fan、Qiaoqiao Xu、Meihua Xie

  DOI：10.1039/c9cc03893k

  日期：——

  first Pd-catalyzed direct C–H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group is described. This reaction exhibits high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles in moderate-to-good yields. The control experiments evidence the generation of acyl radicals via K2S2O8 promoted decarboxylation

  描述了使用酮基直接基团的α-氧代羧酸在C4位上的Pd催化的第一个Pd的吲哚直接C–H酰化反应。该反应显示出高的区域选择性，并具有宽范围的官能团的耐受性，以中等至良好的产率提供了各种酰化的吲哚。对照实验证明了通过K 2 S 2 O 8促进α-氧代羧酸的脱羧作用以及Pd II / Pd IV催化循环的参与产生了酰基基团。重要的是，观察到的合成有用的选择性可用于制备具有抗肿瘤活性的吲哚衍生物作为微管蛋白抑制剂。
• Palladium catalyzed addition of arylboronic acid or indole to nitriles: synthesis of aryl ketones
  作者：Tuluma Das、Amarnath Chakraborty、Amitabha Sarkar

  DOI：10.1016/j.tetlet.2014.11.009

  日期：2014.12

  Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.

  芳基酮可以通过在三氟甲磺酸水溶液中钯催化将芳基硼酸加成到腈中来方便地合成。该催化体系扩展到在稍加修饰的条件下向腈中加入未保护的吲哚，以高收率生产3-酰基吲哚。
• A novel synthesis of<i>N</i>-hydroxy-3-aroylindoles and 3-aroylindoles
  作者：Gabriella Ieronimo、Giovanni Palmisano、Angelo Maspero、Alessandro Marzorati、Luca Scapinello、Norberto Masciocchi、Giancarlo Cravotto、Alessandro Barge、Marco Simonetti、Keshav Lalit Ameta、Kenneth M. Nicholas、Andrea Penoni

  DOI：10.1039/c8ob01471j

  日期：——

  A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.

  通过C-亚硝基芳族化合物与共轭末端炔基的环化反应，可以实现简单的吲哚合成，从而以中等到良好的产率，实现了简单，高度区域选择性，原子和一步经济地获得3-芳基吲哚的方法。研究了吲哚支架的进一步功能化，并获得了合成大麻素JWH-018的简便方法。
• Copper-catalyzed decarboxylative C3-acylation of free (N–H) indoles with α-oxocarboxylic acids
  作者：Cuiping Wang、Shaoyan Wang、Hua Li、Jingbo Yan、Haijun Chi、Xichao Chen、Zhiqiang Zhang

  DOI：10.1039/c3ob42171f

  日期：——

  An efficient Cu-catalyzed decarboxylative C3-acylation of free (N–H) indoles using α-oxocarboxylic acids as acylating agents has been developed. This method was compatible with a variety of functional groups and provided an attractive alternative access to 3-acylindoles in moderate to high yields.

  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。
• A Simple, Effective, Green Method for the Regioselective 3-Acylation of Unprotected Indoles
  作者：Phuong Tran、Hai Tran、Poul Hansen、Mai Do、Thach Le

  DOI：10.3390/molecules201019605

  日期：——

  A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.

  开发了一种快速且绿色方法，用于吲哚3-位选择性酰化而无需保护NH位置。该方法基于使用酸酐的Friedel-Crafts酰化反应。经过优化，发现使用催化量的Y(OTf)3和市售离子液体[BMI]BF4(1-丁基-3-甲基咪唑四氟硼酸盐)作为溶剂效果最佳。反应在单模微波辐射下非常短的时间内完成。该催化剂可重复使用多达四次而不会明显损失活性。研究了一系列取代吲哚作为底物，并合成了十三种新化合物。