7-(4-methoxyphenyl)indole | 777061-22-0

• 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: 7-(4-methoxyphenyl)indole
• 英文别名: 7-(4-methoxyphenyl)-1H-indole
• CAS: 777061-22-0
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: KFWGHAFPIRUNFT-UHFFFAOYSA-N

物化性质

• 熔点：
  103-108 °C
• 沸点：
  425.1±28.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对氯甲苯 、 7-(4-methoxyphenyl)indole 在 Cy-DHTP*HBF₄ 、 palladium diacetate 、 lithium tert-butoxide 作用下， 以 甲苯 为溶剂， 反应 21.0h， 以50%的产率得到7-(4-methoxyphenyl)-3-(p-tolyl)-1H-indole
  参考文献：
  名称：

  钯催化的N-未取代的吲哚与芳基氯化物和三氟甲磺酸酯的直接C3选择性芳基化

  摘要：

  N-未取代的吲哚与芳基氯化物和三氟甲磺酸酯的直接C3-芳基化反应已使用钯-二羟基叔苯基膦（DHTP）催化剂实现。位点选择性不同于其他与结构相关的配体获得的位点选择性。DHTP配体的这一独特特征归因于配体的锂盐与吲哚之间的络合物形成。该方法被应用于具有氯基团的药物的后期衍生化。

  DOI：

  10.1021/acs.orglett.7b02669
• 作为产物：
  描述：

  7-溴吲哚 在 四(三苯基膦)钯 、 potassium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 5.43h， 生成 7-(4-methoxyphenyl)indole
  参考文献：
  名称：

  Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection

  摘要：

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.

  DOI：

  10.1021/jo0491612

文献信息

• Site-Selective Cross-Coupling of Dichlorinated Benzo-Fused Nitrogen-Heterocycles with Grignard Reagents
  作者：Hideyuki Konishi、Tatsuya Itoh、Kei Manabe

  DOI：10.1248/cpb.58.1255

  日期：——

  Site-selective cross-coupling of dihaloarenes constitutes a useful method for synthesis of multi-substituted arenes. In this paper, we report the site-selective cross-coupling of dichlorinated benzo-fused nitrogen-heterocycles having two chloro groups on the benzene ring. These dichlorinated heterocycles reacted with Grignard reagents in the presence of PdCl2(PCy3)2 at the positions ortho to the nitrogen-based substituents with high selectivities. A mechanism in which interaction between Lewis acidic Mg and Cl of the ortho position facilitates C–Cl bond cleavage is proposed.

  二卤芳烃的位点选择性交叉偶联是一种合成多取代芳烃的有效方法。在本文中，我们报告了氮杂环苯并融合的二氯化物的位点选择性交叉偶联，这些化合物在苯环上有两个氯基团。这些二氯化异环化合物在PdCl2(PCy3)2的存在下，与格氏试剂发生反应，反应位置选择性高，主要发生在与氮基取代基邻位。我们提出了一种机制，其中路易斯酸性镁与邻位氯的相互作用促进了C–Cl键的断裂。
• Palladium-Catalyzed Direct C3-Selective Arylation of N-Unsubstituted Indoles with Aryl Chlorides and Triflates
  作者：Miyuki Yamaguchi、Kohei Suzuki、Yusuke Sato、Kei Manabe

  DOI：10.1021/acs.orglett.7b02669

  日期：2017.10.6

  The direct C3-arylation of N-unsubstituted indoles with aryl chlorides and triflates has been realized using a palladium–dihydroxyterphenylphosphine (DHTP) catalyst. The site selectivity is different from that obtained with other structurally related ligands. This unique feature of the DHTP ligand is attributed to complex formation between the lithium salts of the ligand and the indole. The method

  N-未取代的吲哚与芳基氯化物和三氟甲磺酸酯的直接C3-芳基化反应已使用钯-二羟基叔苯基膦（DHTP）催化剂实现。位点选择性不同于其他与结构相关的配体获得的位点选择性。DHTP配体的这一独特特征归因于配体的锂盐与吲哚之间的络合物形成。该方法被应用于具有氯基团的药物的后期衍生化。
• Synthesis of Seven-Membered Azepino[3,2,1-<i>hi</i>]indoles via Rhodium-Catalyzed Regioselective C–H Activation/1,8-Diazabicyclo[5.4.0]undec-7-ene-Catalyzed Intramolecular Amidation of 7-Phenylindoles in One Pot
  作者：Yumeng Yuan、Guoshuai Pan、Xiaofeng Zhang、Buhong Li、Shengchang Xiang、Qiufeng Huang

  DOI：10.1021/acs.joc.9b02289

  日期：2019.11.15

  An unprecedented rhodium-catalyzed regioselective C-H activation/1,8-diazabicyclo[5.4.0]undec-7-ene-catalyzed intramolecular amidation of 7-arylindoles with diazomalonates is described that provides a straightforward route to seven-membered azepino[3,2,1-hi]indoles in good to excellent yields in one pot. A wide range of functional groups, including F, OMe, NPh2, SiMe3, Cl, CN, CHO, COMe, CO2Me, CF3

  前所未有的铑催化的区域选择性CH活化/ 1,8-二氮杂双环[5.4.0]十一碳-7烯催化的7-芳基吲哚与重氮丙二酸酯的分子内酰胺化反应为七元azepino [3,2]提供了直接途径一锅中，1-1-吲哚的产率良好至优异。包括F，OMe，NPh2，SiMe3，Cl，CN，CHO，COMe，CO2Me，CF3和NO2在内的各种官能团均具有良好的耐受性。
• Pyridazine <i>N</i>-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles
  作者：Vinaykumar Kanchupalli、Desna Joseph、Sreenivas Katukojvala

  DOI：10.1021/acs.orglett.5b03064

  日期：2015.12.4

  Pyridazine N-oxides are used for the first time as precursors of metallocarbenes. These nitrogen-rich heterocycles led to the discovery of a novel acceptor and donor-acceptor enalcarbenoids. The synthetic utility of these metallocarbenes was demonstrated in the rhodium-catalyzed denitrogenative transannulation of pyridazine N-oxides with pyrroles to the valuable alkyl, 7-aryl, and 7-styryl indoles. The transannulation strategy was applied to the synthesis of a potent anticancer agent.
• Rhodium-catalyzed direct C H amination of 2-arylindoles and 7-arylindoles with free amines
  作者：Yao Qin、Weihui Zhuang、Xiemin Guo、Xiaofeng Zhang、Qiufeng Huang

  DOI：10.1016/j.tetlet.2020.152686

  日期：2021.1