dimethyl 2-(methyl(phenyl)amino)maleate | 4606-54-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 2-(methyl(phenyl)amino)maleate
• 英文别名: Mkzntkzqczrcqa-pknbqfbnsa-；dimethyl (E)-2-(N-methylanilino)but-2-enedioate
• CAS: 4606-54-6
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: MKZNTKZQCZRCQA-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(methyl(phenyl)amino)maleate 在 甲醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-(hydroxymethyl)-1-methylquinolin-4(1H)-one
  参考文献：
  名称：

  抑制细菌生长和运动的天然和非天然喹诺酮类药物的合成

  摘要：

  最近发现的合成小号甲基化的喹诺酮的天然产物（1）进行，除了产生一系列2取代基-4-喹诺酮衍生物（的2 - 11）。使用了两种方法：(i) N- (酮芳基)酰胺的碱催化环化；(ii) 通过 Suzuki-Miyaura 交叉偶联将取代基连接到喹诺酮核心。还生产了一小组相关的 2(1 H )-喹诺酮 ( 12 – 19 )。对合成的化合物的抗菌特性进行了评估。烯烃取代的 4-喹诺酮8显着抑制了铜绿假单胞菌菌株以及 4-喹诺酮类和 2(1 H )-喹诺酮类均能够抑制枯草芽孢杆菌的蜂群行为。

  DOI：

  10.1021/acs.jnatprod.0c00865
• 作为产物：
  描述：

  4-(N-甲基苯胺基)-4-氧代丁酸 在 rhodium(II) acetate dimer 、 水 、 三乙胺 、 氯甲酸甲酯 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 dimethyl 2-(methyl(phenyl)amino)maleate
  参考文献：
  名称：

  A Novel Cycloaddition Reaction of α-Diazo-γ-amido Ketones Catalyzed by Rhodium(II) Acetate. Scope and Mechanistic Details of the Process

  摘要：

  alpha-Diazo ketones containing an amido group in the gamma-position have been found to undergo a novel rhodium(II)-catalyzed cycloaddition reaction. Intramolecular cyclization of the keto carbenoid onto the oxygen atom of the amide group generates a carbonyl ylide dipole as a transient species. This highly stabilized dipole does not readily undergo 1,3-dipolar cycloaddition but rather transfers a proton to produce a cyclic ketene N,O-acetal. The ketene acetal is unstable to moisture and upon standing is readily hydrolyzed to a gamma-keto delta-lactone and an amine. In the absence of any significant amount of water, the ketene N,O-acetal undergoes conjugate addition with the activated st-bond of the dipolarophile to give a zwitterion intermediate. The anionic portion of the zwitterion adds to the neighboring carbonyl group. This is followed by epoxide ring formation with charge dissipation leading to an amido-substituted spiro cyclopentyl epoxide. In certain cases a hydroxy lactone was also isolated and its formation can be attributed to the competitive hydrolysis of the zwitterionic intermediate. The Rh(II)-catalyzed reaction of the diazo ketoamide derived from N-benzylpiperidone with DMAD afforded two different types of cycloadducts. In addition to the spiro cyclopentyl epoxide, a product derived from trapping of the carbonyl ylide dipole was also obtained, thereby providing additional support for the proposed mechanism.

  DOI：

  10.1021/jo952078h

文献信息

• [EN] QUINOLINONE LYSYL OXIDASE-LIKE 2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS QUINOLINONE DE LA LYSYL OXYDASE-LIKE 2 ET UTILISATIONS DESDITS INHIBITEURS
  申请人：PHARMAKEA INC

  公开号：WO2017139274A1

  公开（公告）日：2017-08-17

  Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

  本文描述了一些具有LOXL2抑制剂作用的化合物，制备这些化合物的方法，包含这些化合物的药物组合物和药物，以及使用这些化合物治疗与LOXL2活性相关的疾病、病症或障碍的方法。
• Quinolinone lysyl oxidase-like 2 inhibitors and uses thereof
  申请人：PHARMAKEA, INC.

  公开号：US10588900B2

  公开（公告）日：2020-03-17

  Described herein are compounds that are LOXL2 inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with LOXL2 activity.

  本文描述了作为 LOXL2 抑制剂的化合物、制造此类化合物的方法、包含此类化合物的药物组合物和药物，以及使用此类化合物治疗与 LOXL2 活性相关的病症、疾病或失调的方法。
• Sheradsky, Tuvia; Nov, Eliahu, Journal of the Chemical Society. Perkin transactions I, 1983, # 3, p. 527 - 530
  作者：Sheradsky, Tuvia、Nov, Eliahu

  DOI：——

  日期：——
• SHERADSKY, T.;NOV, E., J. CHEM. SOC. PERKIN TRANS., 1983, N 3, 527-529
  作者：SHERADSKY, T.、NOV, E.

  DOI：——

  日期：——
• CAIRNS H.; PAYNE A. R., J. HETEROCYCL. CHEM., 1978, 15, NO 4, 551-553
  作者：CAIRNS H.、 PAYNE A. R.

  DOI：——

  日期：——