2-(4-methoxyphenyl)-3-methyl-1H-indole | 5782-15-0

• 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: 2-(4-methoxyphenyl)-3-methyl-1H-indole
• 英文别名: 2-(4-methoxyphenyl)-3-methylindole；2-(4-methoxy-phenyl)-3-methyl-1H-indole
• CAS: 5782-15-0
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: HUODHPNBERMHEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.12
• 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：

  2-(4-methoxyphenyl)-3-methyl-1H-indole 在 吡啶 、 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 苯酚,4-[3-甲基-1-(苯基甲基)-1H-吲哚-2-基]-,乙酸酯(ester)
  参考文献：
  名称：

  2-Phenylindoles. Effect of N-benzylation on estrogen receptor affinity, estrogenic properties, and mammary tumor inhibiting activity

  摘要：

  Hydroxy-2-phenylindoles carrying substituted benzyl groups and similar substituents at the nitrogen were synthesized and tested for their ability to displace estradiol from its receptor. All of the derivatives tested exhibited high binding affinities for the calf uterine estrogen receptor, with RBA values ranging from 0.55 to 16 (estradiol 100). The mouse uterine weight tested revealed only low estrogenicity for this class of compounds. Several derivatives showed antiestrogenic activity with a maximum inhibition of estrone-stimulated uterine growth of 40%. Two of the compounds (6c, 21c) were tested for antitumor activity in dimethylbenanthracene- (DMBA-) induced estrogen-dependent rat mammary tumors. Only the 4-cyanobenzyl derivative 21c was active. After 4 weeks of treatment with 12 mg/kg (6 times/week), the average tumor area was decreased by 57% (control +204%). In vitro, an inhibitory effect of 21b was only observed with hormone-sensitive MCF-7 breast cancer cells but not with hormone-independent MDA-MB 231 cells. These results make a mode of action involving the estrogen receptor system likely.

  DOI：

  10.1021/jm00384a022
• 作为产物：
  描述：

  (2-acetyl-phenylamino)-(4-methoxy-phenyl)-acetic acid 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以46%的产率得到2-(4-methoxyphenyl)-3-methyl-1H-indole
  参考文献：
  名称：

  Substituted Nitrogen Heterocycles and Synthesis and Uses Thereof

  摘要：

  该发明涉及一种化学式为1的氮杂环化合物。还公开了一种合成该化合物的方法，以及利用该化合物治疗各种疾病和病况的用途。

  公开号：

  US20090247766A1

文献信息

• Manganese(<scp>iii</scp>)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides
  作者：Shuai-Shuai Jiang、Yu-Ting Xiao、Yan-Chen Wu、Shu-Zheng Luo、Ren-Jie Song、Jin-Heng Li

  DOI：10.1039/d0ob00877j

  日期：——

  1-a]isoquinolin-6(5H)-ones through manganese(III)-promoted tandem phosphinoylation/cyclization of 2-arylindoles or 2-arylbenzimidazoles with disubstituted phosphine oxides was developed. In this transformation, new C–P bond and C–C bond were constructed simultaneously under silver-free conditions, exhibiting a broad substrate scope. It was noted that not only diarylphosphine oxides but also dialkyl and arylalkyl-phosphine

  一种简单实用的方法，通过锰合成磷酸取代的吲哚[2,1 - a ]异喹啉-6（5 H）-和苯并咪唑[2,1 - a ]异喹啉-6（5 H）-。III）促进了双芳基膦酸酯或2-芳基苯并咪唑与双取代氧化膦的串联膦酰基化/环化反应。在这种转变中，在无银条件下同时构建了新的C–P键和C–C键，具有广泛的底物范围。注意到不仅二芳基膦氧化物，而且二烷基和芳基烷基膦氧化物也符合条件。
• Iron(II) Bromide-Catalyzed Intramolecular C–H Bond Amination [1,2]-Shift Tandem Reactions of Aryl Azides
  作者：Quyen Nguyen、Tuyen Nguyen、Tom G. Driver

  DOI：10.1021/ja3113565

  日期：2013.1.16

  Iron(II) bromide catalyzes the transformation of ortho-substituted aryl azides into 2,3-disubstituted indoles through a tandem ethereal C-H bond amination [1,2]-shift reaction. The preference for the 1,2-shift component of the tandem reaction was established to be Me < 1° < 2° < Ph.

  溴化铁 (II) 通过串联醚 CH 键胺化 [1,2] 转移反应催化邻位取代的芳基叠氮化物转化为 2,3-二取代的吲哚。对串联反应的 1,2-转变组分的偏好确定为 Me < 1° < 2° < Ph。
• Organophotocatalytic Arene Functionalization: C–C and C–B Bond Formation
  作者：Da Seul Lee、Chung Soo Kim、Naila Iqbal、Gyeong Su Park、Kyung-sun Son、Eun Jin Cho

  DOI：10.1021/acs.orglett.9b03877

  日期：2019.12.20

  developed in the presence of an organophotosensitizer, 3,7-di([1,1'-biphenyl]-4-yl)-10-(4-(trifluoromethyl)phenyl)-10H-phenoxazine that has highly negative reduction potential at its photoexcited state. The developed reaction conditions are mild and allow the intermolecular C-C bond formation of the generated aryl radical with electron-rich (hetero)arenes and C-B bond formation with bis(pinacolato)diboron

  在有机光敏剂3,7-二（[[1,1'-联苯] -4-基）-10-（4-（三氟甲基）苯基）存在下，开发了芳基卤化物的有机光催化CC和CB键形成反应。 -10H-吩恶嗪在光激发态下具有极高的负还原电位。发达的反应条件是温和的，并允许生成的芳基与富电子（杂）芳烃形成分子间CC键，并与双（频哪醇）二硼烷形成CB键。
• Mild and selective base-free C–H arylation of heteroarenes: experiment and computation
  作者：Hannes P. L. Gemoets、Indrek Kalvet、Alexander V. Nyuchev、Nico Erdmann、Volker Hessel、Franziska Schoenebeck、Timothy Noël

  DOI：10.1039/c6sc02595a

  日期：——

  A mild and selective C–H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and

  描述了吲哚、苯并呋喃和苯并噻吩的温和选择性 C-H 芳基化策略。芳基化方法使用等摩尔量的芳基重氮盐作为芳基化试剂。该方案操作简单、无碱、耐湿且耐空气。它利用低钯负载量（0.5 至 2.0 mol% Pd）、短反应时间、绿色溶剂（EtOAc/2-MeTHF 或 MeOH）并在室温下进行，提供广泛的底物范围（47 个示例）和出色的选择性（吲哚和苯并呋喃的C-2芳基化，苯并噻吩的C-3芳基化。机理实验和 DFT 计算支持 Heck-Matsuda 型耦合机制。
• Base-promoted domino reaction for the synthesis of 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes
  作者：Yan-Dong Wu、Jun-Rui Ma、Wen-Ming Shu、Kai-Lu Zheng、An-Xin Wu

  DOI：10.1016/j.tet.2016.06.046

  日期：2016.8

  A base-promoted domino reaction to synthesize the 2,3-disubstituted indoles from 2-aminobenzaldehyde/2-amino aryl ketones, tosylhydrazine, and aromatic aldehydes has been developed. This strategy provides a simple and beneficial way for the construction of 2,3-disubstituted indole compounds from readily available starting materials under mild conditions.

  已开发出一种碱促进的多米诺反应，该反应由2-氨基苯甲醛/ 2-氨基芳基酮，甲苯磺酰肼和芳族醛合成2,3-二取代的吲哚。该策略为在温和条件下由容易获得的起始原料构建2，3-二取代的吲哚化合物提供了一种简单而有益的方法。

表征谱图