(5-methoxy-1H-indol-3-yl)(phenyl)methanone | 103608-21-5

• 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-methoxy-1H-indol-3-yl)(phenyl)methanone
• 英文别名: 3-Benzoyl-5-methoxy-1H-indole；(5-methoxy-1H-indol-3-yl)-phenylmethanone
• CAS: 103608-21-5
• 化学式: C₁₆H₁₃NO₂
• mdl: MFCD12541986
• 分子量: 251.285
• InChiKey: WZMXVMOKBVLSPU-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  455.2±25.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-methoxy-1H-indol-3-yl)(phenyl)methanone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以77%的产率得到3-苄基-5-甲氧基-1H-吲哚
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1H-Indoles Using Trialkylboranes

  摘要：

  We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine.

  DOI：

  10.1021/ja0608139
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 在 Jones reagent 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 6.0h， 生成 (5-methoxy-1H-indol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  N-羟基-3-芳酰基吲哚和3-芳酰基吲哚的新颖合成

  摘要：

  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。

  DOI：

  10.1039/c8ob01471j

文献信息

• 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。
• Facile Access to 3-Acylindoles through Palladium-Catalyzed Addition of Indoles to Nitriles: The One-Pot Synthesis of Indenoindolones
  作者：Yuanhong Ma、Jingsong You、Feijie Song

  DOI：10.1002/chem.201203354

  日期：2013.1.21

  The palladium‐catalyzed addition of indoles to nitriles affords 3‐acylindoles. The reaction proceeds with high selectivity, wide substrate scope, broadly available starting materials, and an operationally simple procedure. Combination with the palladium‐catalyzed intramolecular oxidative coupling of 3‐indolylarylketone gives access to indenoindolones in a one‐pot synthesis.

  关联性良好：钯催化的吲哚在腈中的加成反应生成3-acylindoldols。反应以高选择性，广泛的底物范围，广泛可用的起始原料和操作简单的方法进行。与钯催化的3-吲哚基芳基酮的分子内氧化偶合相结合，可在一锅合成中获得茚并吲哚酮。
• 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。
• Synthesis of 3-acylindoles via decarboxylative cross-coupling reaction of free (NH) indoles with α-oxocarboxylic acids
  作者：Li-Jun Gu、Ji-Yan Liu、Li-Zhu Zhang、Yong Xiong、Rui Wang

  DOI：10.1016/j.cclet.2013.10.004

  日期：2014.1

  Abstract A convenient and general method for acylation of free (N H) indoles via palladium-catalyzed decarboxylative cross-coupling reaction was developed. This process provided a useful method for the preparation of diverse 3-acylindoles in high yields utilizing a reaction with readily accessible reactants under mild conditions.

  摘要提出了一种方便，通用的钯催化脱羧交叉偶联反应对游离（NH）吲哚进行酰化的方法。该方法提供了在温和条件下利用与易于获得的反应物的反应以高收率制备各种3-酰基吲哚的有用方法。
• 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。