(R)-N-methyl-3-aminobutyric acid

• 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: (R)-N-methyl-3-aminobutyric acid
• 英文别名: R-N-methyl-3-aminobutyric acid；N-methyl-3-aminobutyric acid；(3R)-3-(methylazaniumyl)butanoate
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: VWQSQYOPIHNGBY-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ent-gentrymine B iodide 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 phosphate buffer 、 乙腈 为溶剂， 反应 2.5h， 生成 (R)-N-methyl-3-aminobutyric acid
  参考文献：
  名称：

  Gentrymine B, an N -Quaternary Ancistrocladus Alkaloid: Stereoanalysis, Synthesis, and Biomimetic Formation from Gentrymine A 1

  摘要：

  The total synthesis of the N-quaternary isoquinoline alkaloid gentrymine B (1) and of its unnatural enantiomer as well as its oxidative degradation is described. A further proof of stereostructure and hints at the biosynthetic origin of the unusual S,S-configuration in gentrymine B (1) were obtained by an additional biomimetic synthesis of 1 from the related-but 1R-configured-natural product gentrymine A (2), by N-methylation and subsequent spontaneous epimerization at C-l. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01054-6

文献信息

• Cyclombandakamines A₁and A₂, Oxygen-Bridged Naphthylisoquinoline Dimers from a Congolese<i>Ancistrocladus</i>Liana
  作者：Blaise Kimbadi Lombe、Torsten Bruhn、Doris Feineis、Virima Mudogo、Reto Brun、Gerhard Bringmann

  DOI：10.1021/acs.orglett.7b00209

  日期：2017.3.17

  Cyclombandakamines A1 (1) and A2 (2), both with an unprecedented pyrane–cyclohexenone–dihydrofuran sequence and six stereocenters and two chiral axes, are the first oxygen-bridged dimeric naphthylisoquinoline alkaloids. They were isolated from the leaves of an as yet unidentified Congolese Ancistrocladus species. Their stereostructures were established by spectroscopic, chemical, and chiroptical methods

  Cyclombandakamines A 1（1）和A 2（2）都是氧桥联的二聚萘基异喹啉生物碱，它们具有前所未有的吡喃-环己烯酮-二氢呋喃序列，并具有六个立体中心和两个手性轴。它们是从尚未鉴定的刚果Ancistrocladus物种的叶子中分离出来的。它们的立体结构是通过光谱，化学和按摩方法结合DFT和TDDFT计算而建立的。它们显然源自“开链”萘基异喹啉二聚体的一系列氧化环化反应，并表现出显着的抗原生动物活性。
• Gentrymine B, an N -Quaternary Ancistrocladus Alkaloid: Stereoanalysis, Synthesis, and Biomimetic Formation from Gentrymine A 1
  作者：Gerhard Bringmann、Michael Ochse、Manuela Michel

  DOI：10.1016/s0040-4020(99)01054-6

  日期：2000.1

  The total synthesis of the N-quaternary isoquinoline alkaloid gentrymine B (1) and of its unnatural enantiomer as well as its oxidative degradation is described. A further proof of stereostructure and hints at the biosynthetic origin of the unusual S,S-configuration in gentrymine B (1) were obtained by an additional biomimetic synthesis of 1 from the related-but 1R-configured-natural product gentrymine A (2), by N-methylation and subsequent spontaneous epimerization at C-l. (C) 2000 Elsevier Science Ltd. All rights reserved.