2-(2,4-dimethoxyphenyl)-1H-indole | 58697-60-2

• 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: 2-(2,4-dimethoxyphenyl)-1H-indole
• CAS: 58697-60-2
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: DQEKVVGJCXMOMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxyphenyl)-1H-indole 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 3-(diphenylphosphino)-2-(2,4-dimethoxyphenyl)-1-methyl-1H-indole
  参考文献：
  名称：

  钯催化的多氟芳烃与甲苯磺酸烯基酯的直接 C-H 烯烃化

  摘要：

  已开发出一种新的吲哚膦配体L1 ，用于钯催化的多氟芳烃与水分和热稳定的甲苯磺酸烯基酯的直接 C-H 烯化。发现采用L1的催化剂体系在该反应中是有效的，具有良好的结构和功能相容性。

  DOI：

  10.1002/ejic.202200288
• 作为产物：
  描述：

  2-{[2,4-bis(methyloxy)phenyl]ethynyl}aniline 以 水 为溶剂， 反应 1.5h， 以50%的产率得到2-(2,4-dimethoxyphenyl)-1H-indole
  参考文献：
  名称：

  Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.09.135

文献信息

• Nitroalkenes as surrogates for cyanomethylium species in a one-pot synthesis of non-symmetric diarylacetonitriles
  作者：Alexander V. Aksenov、Nicolai A. Aksenov、Zarema V. Dzhandigova、Dmitrii A. Aksenov、Michael Rubin

  DOI：10.1039/c5ra20953f

  日期：——

  Nitroalkenes were used as synthetic equivalents of the cyanomethylium cation in a modular, one-pot synthesis of 2-(3-indolyl)acetonitriles and 2,2-diarylacetonitriles involving electrophilic functionalization of aromatic and heteroaromatic C–H bond.

  硝基烯烃被用作氰基甲基阳离子的合成等价物，用于2-（3-吲哚基）乙腈和2,2-二芳基乙腈的模块式一锅合成，涉及芳族和杂芳族CH键的亲电子官能化。
• Modular Counter-Fischer–Indole Synthesis through Radical-Enolate Coupling
  作者：Hyunho Chung、Jeongyun Kim、Gisela A. González-Montiel、Paul Ha-Yeon Cheong、Hong Geun Lee

  DOI：10.1021/acs.orglett.1c00003

  日期：2021.2.5
• 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.
• BAZILE Y.; BRAS J.-P.; COINTET P. DE; NANTHAVONG S.; PIGEROL C.; BROLL M.+, EUR. J. MED. CHEM., 1977, 12, NO 6, 525-530
  作者：BAZILE Y.、 BRAS J.-P.、 COINTET P. DE、 NANTHAVONG S.、 PIGEROL C.、 BROLL M.+

  DOI：——

  日期：——
• US4024155A
  申请人：——

  公开号：US4024155A

  公开（公告）日：1977-05-17