1-(2-phenyl-1H-indol-5-yl)ethanone | 1200659-88-6

• 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: 1-(2-phenyl-1H-indol-5-yl)ethanone
• CAS: 1200659-88-6
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: NPSOXGMUSDOEEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (Z)-N-(4-acetylphenyl)-N-(2-bromo-1-phenylvinyl)cyanamide 在 palladium diacetate 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 8.0h， 以60%的产率得到1-(2-phenyl-1H-indol-5-yl)ethanone
  参考文献：
  名称：

  The sequential reactions of tetrazoles with bromoalkynes for the synthesis of (Z)-N-(2-bromo-1-vinyl)-N-arylcyanamides and 2-arylindoles

  摘要：

  通过四唑与溴炔的 Ag 催化 α-加成-Pd 催化 C-H 键官能化的顺序反应制备了 2-芳基吲哚。在 Ag 催化下，四唑与溴炔发生了立体控制的 α 加成反应，顺利生成了 (Z)-N-（2-溴-1-乙烯基）-N-芳基氰酰胺，随后通过 Pd 催化的直接 C-H 键官能化反应将其分子内环化为 2-芳基吲哚。

  DOI：

  10.1039/c3ra40669e

文献信息

• Microwave-assisted synthesis of indole- and azaindole-derivatives in water via cycloisomerization of 2-alkynylanilines and alkynylpyridinamines promoted by amines or catalytic amounts of neutral or basic salts
  作者：Adriano Carpita、Arianna Ribecai、Paolo Stabile

  DOI：10.1016/j.tet.2010.06.083

  日期：2010.8

  An efficient methodology is described and exploited for the preparation of differently substituted indoles and azaindoles via microwave-assisted cycloisomerization in water of 2-alkynylanilines and alkynylpyridinamines, which is promoted by catalytic amounts of neutral or basic salts or by stoichiometric weak organic bases. Good to high yields in the cyclization can be achieved for a variety of 2-amino (hetero)aryl alkynes. Reactions are run without any added metal catalyst. A comparison with the cycloisomerization conducted under conventional heating is also described. (C) 2010 Elsevier Ltd. All rights reserved.
• Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases
  作者：Adriano Carpita、Arianna Ribecai

  DOI：10.1016/j.tetlet.2009.09.135

  日期：2009.12

  An unprecedented green methodology is described for the preparation of differently substituted indoles via microwave-assisted cycloisomerization of 2-alkynylaniline derivatives in water. Moderate to good yields in the cyclization can be achieved for a variety of 2-aminoaryl alkynes. Reactions are run without any added metal catalyst, acid, or base, and do not take place by applying conventional heating. (C) 2009 Elsevier Ltd. All rights reserved.
• PIPERAZINE DERIVATIVES AS MAGL INHIBITORS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3694840B1

  公开（公告）日：2021-08-04
• The sequential reactions of tetrazoles with bromoalkynes for the synthesis of (Z)-N-(2-bromo-1-vinyl)-N-arylcyanamides and 2-arylindoles
  作者：Jiajun Zhang、Ling-Guo Meng、Pinhua Li、Lei Wang

  DOI：10.1039/c3ra40669e

  日期：——

  2-Arylindoles were prepared by a sequential reaction of Ag-catalyzed α-addition–Pd-catalyzed C–H bond functionalization of tetrazoles with bromoalkynes. A stereocontrolled Ag-catalyzed α-addition reaction of tetrazoles with bromoalkynes underwent smoothly to generate (Z)-N-(2-bromo-1-vinyl)-N-arylcyanamides, which were subsequently converted into 2-arylindoles through an intramolecular cyclization by Pd-catalyzed direct C–H bond functionalizations.

  通过四唑与溴炔的 Ag 催化 α-加成-Pd 催化 C-H 键官能化的顺序反应制备了 2-芳基吲哚。在 Ag 催化下，四唑与溴炔发生了立体控制的 α 加成反应，顺利生成了 (Z)-N-（2-溴-1-乙烯基）-N-芳基氰酰胺，随后通过 Pd 催化的直接 C-H 键官能化反应将其分子内环化为 2-芳基吲哚。