3-(N-Methyl-N-α-methylbenzylcarbamoyl)-1,2,4-trimethylquinolinium | 104785-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(N-Methyl-N-α-methylbenzylcarbamoyl)-1,2,4-trimethylquinolinium
• 英文别名: N,1,2,4-tetramethyl-N-[(1R)-1-phenylethyl]quinolin-1-ium-3-carboxamide
• CAS: 104785-61-7
• 化学式: C₂₂H₂₅N₂O
• 分子量: 333.453
• InChiKey: OEDUOLPQUJLSSA-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  24.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline 在 四氯苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 3-(N-Methyl-N-α-methylbenzylcarbamoyl)-1,2,4-trimethylquinolinium
  参考文献：
  名称：

  NAD(P)+-NAD(P)H models. 61. An interconversion between central and axial chiralities as evidence for a functional model of chemical evolution of an enzyme

  摘要：

  DOI：

  10.1021/ja00280a080

文献信息

• NAD(P)H-NAD(P)⁺Models. 73. Structure-Stereochemistry Relationship in the Reaction of NAD Analog
  作者：Atsuyoshi Ohno、Yuji Mikata、Mutsuo Goto、Takeshi Kashiwagi、Takanori Tanaka、Masami Sawada

  DOI：10.1246/bcsj.64.81

  日期：1991.1

  different NAD(P)H analogs have been oxidized by various substituted and unsubstituted 1,4-benzoquinones in the presence or absence of magnesium ion. The stereospecificity of the reaction depends not only on the reactivity of quinone but also on that of the analogs as well as on the presence or absence of magnesium ion. The results are discussed from the viewpoint of reaction mechanism for the transfer of

  在镁离子存在或不存在的情况下，四种不同的 NAD(P)H 类似物已被各种取代和未取代的 1,4-苯醌氧化。反应的立体特异性不仅取决于醌的反应性，还取决于类似物的反应性以及镁离子的存在与否。从转移（净）氢阴离子的反应机理的角度讨论了结果。
• NAD(P)⁺–NAD(P)H Models. 81. Temperature-Dependent Stereospecificity in the Interconversion between Central and Axial Chiralities
  作者：Mutsuo Okamura、Yuji Mikata、Norimasa Yamazaki、Akihiro Tsutsumi、Atsuyoshi Ohno

  DOI：10.1246/bcsj.66.1191

  日期：1993.4

  In the oxidation of (4R)-Me3MQPH or (4R)-Me3PNPH with a series of 1,4-benzoquinone and its derivatives, the R/S ratio with respect to the axial chirality in the product, i.e., 11R-/11S- isomer ratio in Me3MQP+ or 7R-/7S- isomer ratio in Me3PNP+, changes depending on the reaction temperature as well as the reactivity of quinone. It is confirmed that kinetic R-preference stems from the entropy-control

  在 (4R)-Me3MQPH 或 (4R)-Me3PNPH 与一系列 1,4-苯醌及其衍生物的氧化中，R/S 比相对于产物中的轴向手性，即 11R-/11S- Me3MQP+ 中的异构体比例或 Me3PNP+ 中的 7R-/7S- 异构体比例随反应温度以及醌的反应性而变化。证实了动力学R偏好源于熵控制，而动力学S偏好来自于焓控制。焓和熵的相对重要性是根据初始电子转移步骤中过渡态的早和晚来讨论的。
• NAD(P)⁺–NAD(P)H Models. 82. Effect of Magnesium Ion on the Stereospecificity and Conformations at the Ground and Transition States of the Reaction
  作者：Mutsuo Okamura、Yuji Mikata、Norimasa Yamazaki、Akihiro Tsutsumi、Atsuyoshi Ohno

  DOI：10.1246/bcsj.66.1197

  日期：1993.4

  the presence and absence of magnesium ion have been studied. The major conformation at the ground state of Me3MQPH changes largely when this molecule forms a complex with a magnesium ion. The conformations at the ground and transition states will be discussed in relation to the stereospecificity of the reaction of this compound with quinones.

  已经研究了 3-[甲基(α-甲基苄基)氨基甲酰基]-1,2,4-三甲基-1,4-二氢喹啉 ((4R)-Me3MQPH) 在镁离子存在和不存在下的构象。当该分子与镁离子形成复合物时，Me3MQPH 基态的主要构象发生很大变化。基态和过渡态的构象将与该化合物与醌反应的立体特异性进行讨论。
• Stereospecific Electrochemical Oxidation of NAD(P)H Analogs Mediated by Radical Cation of Anilines
  作者：Mutsuo Okamura、Takeshi Kashiwagi、Yuji Mikata、Norimasa Yamazaki、Atsuyoshi Ohno

  DOI：10.1246/cl.1992.1247

  日期：1992.7

  Net hydrogen-atom (H•) transfer was observed in electrochemical oxidation of NAD(P)H analogs in the presence of aniline or its derivatives. The reaction mechanism is discussed on the basis of stereospecificities.

  在苯胺或其衍生物存在的情况下，NAD（P）H类似物在电化学氧化过程中观察到氢原子（H•）的净转移。根据立体选择性讨论了反应机理。
• NAD(P)+-NAD(P)H models. 61. An interconversion between central and axial chiralities as evidence for a functional model of chemical evolution of an enzyme
  作者：Atsuyoshi. Ohno、Meguru. Ohara、Shinzaburo. Oka

  DOI：10.1021/ja00280a080

  日期：1986.10