3,4-二甲氧基-N-(2-甲基丙基)苯胺 | 649763-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4-二甲氧基-N-(2-甲基丙基)苯胺
• 英文名称: N-isobutyl-3,4-dimethoxyaniline
• 英文别名: 3,4-Dimethoxy-N-(2-methylpropyl)aniline
• CAS: 649763-34-8
• 化学式: C₁₂H₁₉NO₂
• mdl: MFCD11142899
• 分子量: 209.288
• InChiKey: CSFFYOFLHBAGLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基-N-(2-甲基丙基)苯胺 在 溶剂黄146 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.5h， 生成 7,8-dimethoxy-N(10)-isobutylisoalloxazine-N(5)-oxide
  参考文献：
  名称：

  Model Systems for Flavoenzyme Activity:  Relationships between Cofactor Structure, Binding and Redox Properties

  摘要：

  A series of flavins were synthesized bearing electron-withdrawing and -donating substituents. The electrochemical properties of these flavins in a nonpolar solvent were determined. The recognition of these flavins by a diamidopyridine (DAP) receptor and the effect this receptor has on flavin redox potential was also quantified. It was found that the DAP-flavin binding affinity and the reduction potentials (E-1/2) for both the DAP-bound and unbound flavins correlated well with functions derived from linear free energy relationships (LFERs). These results provide insight and predictive capability for the interplay of electronics and redox state-specific interactions for both abiotic and enzymatic systems.

  DOI：

  10.1021/ja036940b
• 作为产物：
  描述：

  3,4-二甲氧基苯胺 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3,4-二甲氧基-N-(2-甲基丙基)苯胺
  参考文献：
  名称：

  在机理理解的指导下将脱氮黄素调整为高效还原光催化剂——通过内部重原子效应增强关键步骤

  摘要：

  受到大自然的启发并基于机理理解，我们设计了具有与 Li 相当的还原能力的脱氮黄素 (dFl)，其通过独立于分子氧的连续光诱导电子转移 ( con PET) 机制发挥作用。通过将溴引入光催化剂而产生的内部重原子效应（IHAE）通过三重态自由基对显着增强了关键的三重态途径。此外，需要最佳浓度的牺牲电子供体（S sac ）来绕过通过单重态自由基对的非生产性反应。

  DOI：

  10.1002/chem.202200768

文献信息

• Discovery of Conformationally Restricted Human Glutaminyl Cyclase Inhibitors as Potent Anti-Alzheimer’s Agents by Structure-Based Design
  作者：Van-Hai Hoang、Van T. H. Ngo、Minghua Cui、Nguyen Van Manh、Phuong-Thao Tran、Jihyae Ann、Hee-Jin Ha、Hee Kim、Kwanghyun Choi、Young-Ho Kim、Hyerim Chang、Stephani Joy Y. Macalino、Jiyoun Lee、Sun Choi、Jeewoo Lee

  DOI：10.1021/acs.jmedchem.9b00751

  日期：2019.9.12

  analyses indicated that conformationally restrained inhibitors demonstrated much improved QC inhibition in vitro compared to nonrestricted analogues, and several selected compounds demonstrated desirable therapeutic activity in an AD mouse model. The conformational analysis of a representative inhibitor indicated that the inhibitor appeared to maintain the Z-E conformation at the active site, as it

  阿尔茨海默氏病（AD）是一种无法治愈的进行性神经退行性疾病，其发病机理不能由一个单一因素定义，而是由多种因素组成。因此，呼吁寻求替代方法来解决AD的多方面问题。在潜在的替代目标中，我们的目标是集中在谷氨酰胺环化酶（QC）上，该酶可降低AD患者大脑中β-淀粉样蛋白的毒性焦磷酸型。基于原型抑制剂1的假定的活性构象，开发了一系列的N-取代的硫脲，脲和α-取代的酰胺衍生物。结构-活性关系分析表明，与非限制性类似物相比，构象受限的抑制剂在体外表现出大大改善的QC抑制作用，几种选择的化合物在AD小鼠模型中显示出理想的治疗活性。对代表性抑制剂的构象分析表明，该抑制剂似乎在活性位点保持ZE构象，因为它对其有效活性至关重要。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS DE L'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2004069823A1

  公开（公告）日：2004-08-19

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  该发明涉及抑制组蛋白去乙酰化酶的技术。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和病症的组合物和方法。
• Site‐Selective Radical Aromatic C–H Functionalization of Alloxazine and Flavin through Ground‐State Single Electron Transfer
  作者：Agnideep Das、Oscar Charpentier、Cheriehan Hessin、Jules Schleinitz、David Pianca、Nolwenn Le Breton、Sylvie Choua、Laurence Grimaud、Christophe Gourlaouen、Marine Desage-El Murr

  DOI：10.1002/anie.202403417

  日期：——

  Selective functionalization of flavin analogues is desirable for property tuning but requires de novo synthesis. A synthetic strategy involving the introduction of a remote redox site followed by copper complexation turns an alloxazine and a flavin into redox-active structures and activates their aromatic ring for site-selective aromatic C−H functionalization. This unprecedented mechanism opens new

  黄素类似物的选择性官能化对于性能调节是理想的，但需要从头合成。一种合成策略，涉及引入远程氧化还原位点，然后进行铜络合，将咯嗪和黄素转化为氧化还原活性结构，并激活它们的芳环，以实现位点选择性芳族 C−H 官能化。这种前所未有的机制为黄素及其类似物的化学打开了新的前景。
• Model Systems for Flavoenzyme Activity:  Relationships between Cofactor Structure, Binding and Redox Properties
  作者：Yves-Marie Legrand、Mark Gray、Graeme Cooke、Vincent M. Rotello

  DOI：10.1021/ja036940b

  日期：2003.12.1

  A series of flavins were synthesized bearing electron-withdrawing and -donating substituents. The electrochemical properties of these flavins in a nonpolar solvent were determined. The recognition of these flavins by a diamidopyridine (DAP) receptor and the effect this receptor has on flavin redox potential was also quantified. It was found that the DAP-flavin binding affinity and the reduction potentials (E-1/2) for both the DAP-bound and unbound flavins correlated well with functions derived from linear free energy relationships (LFERs). These results provide insight and predictive capability for the interplay of electronics and redox state-specific interactions for both abiotic and enzymatic systems.
• Tuning Deazaflavins Towards Highly Potent Reducing Photocatalysts Guided by Mechanistic Understanding – Enhancement of the Key Step by the Internal Heavy Atom Effect
  作者：Tetiana Pavlovska、David Král Lesný、Eva Svobodová、Irena Hoskovcová、Nataliya Archipowa、Roger Jan Kutta、Radek Cibulka

  DOI：10.1002/chem.202200768

  日期：2022.8.16

  Inspired by nature and based on mechanistic understanding, we designed deazaflavins (dFl) with reducing powers comparable to Li which function via the consecutive photo-induced electron transfer (conPET) mechanism independently on molecular oxygen. The internal heavy atom effect (IHAE) by introducing bromine into the photocatalyst enhances considerably the key triplet pathway via a triplet-born radical

  受到大自然的启发并基于机理理解，我们设计了具有与 Li 相当的还原能力的脱氮黄素 (dFl)，其通过独立于分子氧的连续光诱导电子转移 ( con PET) 机制发挥作用。通过将溴引入光催化剂而产生的内部重原子效应（IHAE）通过三重态自由基对显着增强了关键的三重态途径。此外，需要最佳浓度的牺牲电子供体（S sac ）来绕过通过单重态自由基对的非生产性反应。