1-甲基-4-苯基甲氧基吲哚-3-甲醛 | 93315-78-7

• 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
• 中文名称: 1-甲基-4-苯基甲氧基吲哚-3-甲醛
• 英文名称: 4-benzyloxy-1-methyl-1H-indole-3-carbaldehyde
• 英文别名: 4-(benzyloxy)-1-methyl-1H-indole-3-carbaldehyde；1-methyl-4-phenylmethoxyindole-3-carbaldehyde
• CAS: 93315-78-7
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: WHUYRJAYTFBLLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基-4-苯基甲氧基吲哚-3-甲醛 在 水 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到4-hydroxy-1-methyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  WO2007/241

  摘要：

  公开号：
• 作为产物：
  描述：

  四甲基乙二胺 、 4-(苄氧基)-1-甲基-1H-吲哚 在 水 、 氧气 、 potassium iodide 作用下， 以 乙腈 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 48.0h， 以54%的产率得到1-甲基-4-苯基甲氧基吲哚-3-甲醛
  参考文献：
  名称：

  偶联微孔聚合物上吲哚的可见光驱动C-3功能化

  摘要：

  不含金属的多相有机光催化剂为传统的基于金属的催化剂提供了一种环境友好的替代品。本文报道了一系列具有可调氧化还原电位的咔唑基共轭微孔聚合物（CMP），并探讨了它们在吲哚的C-3甲酰化和硫氰化方面的光催化性能。共轭聚合物是通过FeCl 3介导的Friedel-Crafts反应合成的，它们的氧化还原电势通过简单地改变核的性质（即1,4-二苄基，1,3,5-三苄基或1,3， 5-triazin-2,4,6-triyl）。所得的CMP具有较高的表面积，可见光吸收率和可调的半导体范围带隙。具有最高氧化能力的CMP-CSU6衍生自1,3,5-tri（9 H-咔唑-9-基）苯在室温下对吲哚的C-3甲酰化和硫氰化反应显示出最高的效率。值得注意的是，所制得的催化剂可以容易地回收并保持良好的光催化活性，并且可以重复使用至少五次，这表明其具有良好的可回收性。这些结果对于构建具有可调光氧化还原电势的高性能多孔聚合物

  DOI：

  10.1021/acscatal.8b01478

文献信息

• Catalyst- and Substituent-Controlled Regio- and Stereoselective Synthesis of Indolyl Acrylates by Lewis-Acid-Catalyzed Direct Functionalization of 3-Formylindoles with Diazo Esters
  作者：Sana Jamshaid、Shreedhar Devkota、Yong Rok Lee

  DOI：10.1021/acs.orglett.1c00277

  日期：2021.3.19

  A facile and efficient In(OTf)3- and BF3·OEt2-catalyzed direct transformation of 3-formylindoles with diazo esters has been developed for synthesizing diverse and functionalized indolyl acrylates. This one-pot protocol furnishes various (Z)-α-hydroxy-β-indolyl acrylates, (E)-β-(2-alkoxy-2-oxoethoxy)-α-indolyl acrylates, and (Z)-3-hydroxy-2-indolyl acrylates by a catalyst- and substituent-controlled

  已开发了一种重氮化合物，可以轻松，高效地用In（OTf）3-和BF 3 ·OEt 2催化3-甲酰基吲哚的直接转化，以合成各种功能化的丙烯酸吲哚酯。此一锅操作方案可提供各种（Z）-α-羟基-β-吲哚基丙烯酸酯，（E）-β-（2-烷氧基-2-氧代乙氧基）-α-吲哚基丙烯酸酯和（Z）-3-羟基-丙烯酸酯丙烯酸2-吲哚基酯通过催化剂和取代基控制的区域和立体选择性级联反应。该方案具有几个优点，包括催化剂的低负载，温和的反应条件，范围宽和官能团耐受性高。合成的化合物可以进一步转化为多种功能化的材料。
• Towards Total Synthesis of Communesins and Perophoramidine: Unexpected Cascade Reaction of Michael-Mannich-Mannich Additions
  作者：Yong Qin、Haoxing Wu、Xue Xiao

  DOI：10.1055/s-0030-1259705

  日期：2011.4

  A new type of chiral amidinobenzodiene 5 was prepared from isatin in ten steps. While attempting to prepare the core structure from 5 and tryptamine derivative 17 via a hetero Diels-Alder reaction for the total synthesis of communesin and perophoramidine, we observed an unexpected three-step, one-pot cascade reaction of Michael-Manich-Manich additions. The cascade reaction between 5 and 17 yielded diasteromers 21a and 21b with a complex polycyclic skeleton of 2,3,4,5-diindolinohexahydropyrrole in 76% yield and a ratio of 3:1. The stereochemistry of 21a was confirmed by X-ray crystal-structural analysis.

  通过十步反应，从靛红制备了一种新型的手性脒基苯并二烯5。在尝试通过异构Diels-Alder反应从5和色胺衍生物17制备核心结构，以实现共苷素和perophoramidine的全合成时，我们观察到了一种意外的Michael-Manich-Manich加成三步一锅级联反应。5和17之间的级联反应产生了具有2,3,4,5-二吲哚六氢吡咯复杂多环骨架的21a和21b非对映异构体，产率为76%，比例为3:1。21a的立体化学结构通过X射线晶体结构分析得到了证实。
• Heteroaryl-O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1
  作者：Xiaoyan Zhang、Maud Urbanski、Mona Patel、Roxanne E. Zeck、Geoffrey G. Cox、Haiyan Bian、Bruce R. Conway、Mary Pat Beavers、Philip J. Rybczynski、Keith T. Demarest

  DOI：10.1016/j.bmcl.2005.08.067

  日期：2005.12

  A series of benzo-fused heteroaryl-O-glucosides was synthesized and evaluated in SGLT1 and 2 cell-based functional assays. Indole-O-glucoside 10a and benzimidazole-O-glucoside 18 exhibited potent in vitro SGLT2 inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Aerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction
  作者：Xiang Li、Xiangyong Gu、Yongjuan Li、Pixu Li

  DOI：10.1021/cs5005129

  日期：2014.6.6

  An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.
• Pyrazolone-based anaplastic lymphoma kinase (ALK) inhibitors: Control of selectivity by a benzyloxy group
  作者：Rabindranath Tripathy、Robert J. McHugh、Arup K. Ghose、Gregory R. Ott、Thelma S. Angeles、Mark S. Albom、Zeck Huang、Lisa D. Aimone、Mangeng Cheng、Bruce D. Dorsey

  DOI：10.1016/j.bmcl.2011.10.055

  日期：2011.12

  Anaplastic lymphoma kinase (ALK) is transmembrane receptor tyrosine kinase, with oncogenic variants that have been implicated in ALCL, NSCLC and other cancers. Screening of a VEGFR2-biased kinase library resulted in identification of 1 which showed cross-reactivity with ALK. SAR on the indole segment of 1 showed that a subtle structural modification (the ethoxy group of 1 changed to a benzyloxy to generate 5a) enhanced potency (ALK), selectivity for VEGFR2 and IR along with improvement in metabolic stability. From docking studies of ALK versus VEGFR2 kinase, we postulated that the loss of entropy of the VEGFR2 in the bound form with 5a might be the origin of the reduced activity against that protein. Modification of the heterocyclic segment showed that thiazole-bearing pyrazolones preserved enzyme potency, and enhanced inhibition of NPM-ALK autophosphorylation in ALK-positive ALCL cells (Karpas-299). SAR of the benzyloxy group resulted in compounds which demonstrated good cellular potency in Karpas-299 cells. Compound 8 showed best overall profile for the series with broad kinome selectivity and liver micorsome stability. Compound 8 showed reasonable iv PK in rat, but with little oral exposure. (C) 2011 Elsevier Ltd. All rights reserved.