(3-bromophenyl)(1H-indol-3-yl)methanone | 1096981-81-5

• 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: (3-bromophenyl)(1H-indol-3-yl)methanone
• 英文别名: (3-bromophenyl)-(1H-indol-3-yl)methanone
• CAS: 1096981-81-5
• 化学式: C₁₅H₁₀BrNO
• mdl: MFCD11545373
• 分子量: 300.154
• InChiKey: YKALKDRUOYXFEE-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：
  0.0
• 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 、 间溴苯甲腈 在 2,2'-联吡啶 、 D(+)-10-樟脑磺酸 、 水 、 palladium diacetate 作用下， 反应 36.0h， 以91%的产率得到(3-bromophenyl)(1H-indol-3-yl)methanone
  参考文献：
  名称：

  钯催化游离（NH）吲哚与腈的酰化酰化反应合成3-乙酰基

  摘要：

  已经开发了使用游离的（NH）吲哚和腈有效地钯催化合成3-acylindoles的方法。在Pd（OAc）2 / 2,2'-联吡啶体系下，以d -（+）-樟脑磺酸为添加剂，酰化反应进展顺利。提出了一种可能的机制，涉及腈的碳咔巴定化和随后的酮亚胺水解。

  DOI：

  10.1021/ol303440y

文献信息

• 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。
• Decarboxylative acylation of <i>N</i>-free indoles enabled by a catalytic amount of copper catalyst and liquid-assisted grinding
  作者：Jingbo Yu、Chao Zhang、Xinjie Yang、Weike Su

  DOI：10.1039/c9ob00622b

  日期：——

  A facile decarboxylative acylation of N-free indoles with α-ketonates via liquid-assisted grinding was reported. The reaction requires only a catalytic amount of Cu(OAc)2·H2O in combination with O2 as the terminal oxidant to give various 3-acylindoles with high efficiency. Additionally, this new methodology was applicable to a gram-scale synthesis.

  报道了通过液体辅助研磨将无氮吲哚与α-酮类化合物容易地脱羧酰化。该反应仅需要催化量的Cu（OAc）2 ·H 2 O与作为末端氧化剂的O 2结合就可以高效地得到各种3-酰基环。此外，这种新方法适用于克级合成。
• Synthesis of 3-Aroylindoles as Intermediates of Cannabimimetics and Elucidation of Their Physicochemical Properties
  作者：Hideyo Takahashi、Koji Araki、Kosho Makino、Hidetsugu Tabata、Hiroshi Nakayama、Kei Zaitsu、Tetsuta Oshitari、Hideaki Natsugari

  DOI：10.3987/com-18-13888

  日期：——

  In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the H-1 NMR spectra of 3-(2'-substituted)-benzoyl-2-methylindoles had interesting features. We investigated their physicochemical properties based on VT-NMR, and it was revealed that conformer A (s-trans) is present in preference to conformer B in these compounds.
• Synthesis of 3-Acylindoles by Palladium-Catalyzed Acylation of Free (N–H) Indoles with Nitriles
  作者：Tao-Shan Jiang、Guan-Wu Wang

  DOI：10.1021/ol303440y

  日期：2013.2.15

  An efficient palladium-catalyzed synthesis of 3-acylindoles using free (N–H) indoles and nitriles has been developed. The acylation reaction proceeded well under the Pd(OAc)2/2,2′-bipyridine system and with d-(+)-camphorsulfonic acid as the additive. A possible mechanism involving carbopalladation of nitriles and subsequent hydrolysis of ketimines is proposed.

  已经开发了使用游离的（NH）吲哚和腈有效地钯催化合成3-acylindoles的方法。在Pd（OAc）2 / 2,2'-联吡啶体系下，以d -（+）-樟脑磺酸为添加剂，酰化反应进展顺利。提出了一种可能的机制，涉及腈的碳咔巴定化和随后的酮亚胺水解。