methyl 4,5-dimethoxy-2-(methylamino)benzoate | 350228-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4,5-dimethoxy-2-(methylamino)benzoate
• CAS: 350228-61-4
• 化学式: C₁₁H₁₅NO₄
• mdl: MFCD20132269
• 分子量: 225.244
• InChiKey: PENMFYMTGLWVNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4,5-dimethoxy-2-(methylamino)benzoate 在 哌啶 、 Co(dmgH)(dmgH₂)Cl₂ 、 (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以96%的产率得到2-氨基-4,5-二甲氧基苯甲酸甲酯
  参考文献：
  名称：

  反向电子转移的最小化使得仲苯胺难以捉摸的 sp3 C−H 官能化

  摘要：

  苯胺是光诱导电子转移中最常用的一类底物。 N,N-二烷基衍生物能够通过氧化然后去质子化使 N 原子产生自由基 α。然而，由于快速反电子转移（BET），这种方法对于单取代苯胺来说难以捉摸。在这里，我们证明了在外源烷基胺存在的情况下使用光氧化还原催化可以最大限度地减少 BET。这种方法协同帮助苯胺 SET 氧化，然后加速随后的去质子化。通过这种方式，现在可以生成 α-苯胺烷基自由基，并且这些物质可以在一般意义上用于实现不同的 sp 3 C−H 官能化。

  DOI：

  10.1002/anie.202100051
• 作为产物：
  描述：

  methyl 2-(formylamino)-4,5-dimethoxybenzoate 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以0.5 g的产率得到methyl 4,5-dimethoxy-2-(methylamino)benzoate
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of Bicyclic Substituted Hexahydrobenz[e]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia

  摘要：

  In search of a uroselective alpha (1A) subtype selective antagonist, a novel series of 6-OMe hexahydrobenz [e]isoindoles attached to a bicyclic heterocyclic moiety via a two-carbon linker was synthesized. It was found that in contrast to the previously described series of tricyclic heterocycles,l this bicyclic series has very specific requirements for the heterocyclic attachments. The most important structural features contributing to the alpha (1A)/alpha (1B) selectivity of these compounds were identified. In vitro functional assays for the al adrenoceptor subtypes were used to further characterize the most selective compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity. Compound 48 showed the highest degree of selectivity in the radioligand binding assays (56-fold), in the in vitro functional tests (80-fold), and for in vivo prostate selectivity (960-fold).

  DOI：

  10.1021/jm000541z

文献信息

• Chemo- and Diastereoselective Acylfluorination of Nonactivated Olefins to Access Benzo[<i>b</i>]azepines
  作者：Xingfeng Liu、Yuxi Wang、Tao Xu

  DOI：10.1021/acs.orglett.2c04082

  日期：2023.2.10

  Here, we describe a transition-metal-free condition that realized the intramolecular acylfluorination of unactivated olefins. It was designed to access seven-membered-ring-containing benzo[b]annulenones from readily prepared 2-allylamino benzoic acids. The formation of a broad scope of electronically and sterically varied benzo[b]annulenones was demonstrated (>30 examples, up to 88% yield and >20:1

  在这里，我们描述了一种无过渡金属的条件，该条件实现了未活化烯烃的分子内酰基氟化。它旨在从易于制备的 2-烯丙基氨基苯甲酸中获取含有七元环的苯并 [ b ] 环烯酮。证明了电子和空间变化范围广泛的苯并 [ b ] 环烯酮的形成（>30 个实例，高达 88% 的产率和 >20:1 的 dr 比率）。机理研究表明，原位形成的 XatlFluor-E 活化酸酐是活性物质，可诱导亲电子 7-内触发环化，随后是阳离子的氟化物捕获。
• Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer
  作者：Lei Wang、Kun Fang、Junfei Cheng、Yu Li、Yahui Huang、Shuqiang Chen、Guoqiang Dong、Shanchao Wu、Chunquan Sheng

  DOI：10.1021/acs.jmedchem.9b01626

  日期：2020.1.23

  Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.
• Quinolone–benzylpiperidine derivatives as novel acetylcholinesterase inhibitor and antioxidant hybrids for Alzheimer Disease
  作者：Marc Pudlo、Vincent Luzet、Lhassane Ismaïli、Isabelle Tomassoli、Anne Iutzeler、Bernard Refouvelet

  DOI：10.1016/j.bmc.2014.02.046

  日期：2014.4

  Design, synthesis and evaluation of new acetylcholinesterase inhibitors by combining quinolinecarboxamide to a benzylpiperidine moiety are described. Then, a series of hybrids have been developed by introducing radical scavengers. Molecular modeling was performed and structure activity relationships are discussed. Among the series, most potent compounds show effective AchE inhibitions, high selectivities over butyrylcholinesterase and high radical scavenging activities. On the basis of this work, the ability of quinolone derivatives to serve in the design of N-benzylpiperidine linked multipotent molecules for the treatment of Alzheimer Disease has been established. (C) 2014 Elsevier Ltd. All rights reserved.
• CN115677601
  申请人：——

  公开号：——

  公开（公告）日：——
• Minimization of Back‐Electron Transfer Enables the Elusive sp ³ C−H Functionalization of Secondary Anilines
  作者：Huaibo Zhao、Daniele Leonori

  DOI：10.1002/anie.202100051

  日期：2021.3.29

  Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N‐Dialkyl‐derivatives enable radical generation α to the N‐atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back‐electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence

  苯胺是光诱导电子转移中最常用的一类底物。 N,N-二烷基衍生物能够通过氧化然后去质子化使 N 原子产生自由基 α。然而，由于快速反电子转移（BET），这种方法对于单取代苯胺来说难以捉摸。在这里，我们证明了在外源烷基胺存在的情况下使用光氧化还原催化可以最大限度地减少 BET。这种方法协同帮助苯胺 SET 氧化，然后加速随后的去质子化。通过这种方式，现在可以生成 α-苯胺烷基自由基，并且这些物质可以在一般意义上用于实现不同的 sp 3 C−H 官能化。