(8S,9R,10S)-myrionine | 951681-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: (8S,9R,10S)-myrionine
• 英文别名: (-)-myrionine；myrionine；1-[[(4aS,8S,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydroquinolin-8-yl]methyl]piperidin-2-one
• CAS: 951681-61-1
• 化学式: C₁₅H₂₆N₂O
• 分子量: 250.384
• InChiKey: ARSLSYYPGHBQKL-KCQAQPDRSA-N

物化性质

• 沸点：
  411.5±18.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8S,9R,10S)-myrionine 在 三氯氧磷 、 ammonium hydroxide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以97%的产率得到(-)-myrionidine
  参考文献：
  名称：

  从Myrioneuron nutans合成（-）-甲硫氨酸和（-）-schoberine抗疟疾生物碱的结构和总合成。

  摘要：

  从Myrioneuron nutan（茜草科）及其结构是通过光谱分析（包括质谱和2D NMR）确定的。进行了（-）-myrionidine（1），（-）-schoberine（3），其对映异构体以及9-epimers衍生物的总不对称合成，从而确定了其与Myrionamide（2的绝对构型）的绝对构型）。（-）-Myrionidine（1）及其合成对映异构体（18）对恶性疟原虫具有显着的抗疟活性。

  DOI：

  10.1021/jo801046j
• 作为产物：
  描述：

  (4 aS,8R,8aR)-8-(hydroxymethyl)decahydroquinoline 在 palladium on activated charcoal 氢气 、 potassium hydride 、 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 (8S,9R,10S)-myrionine
  参考文献：
  名称：

  Solution and Crystal Conformations of Myrionine, a New 8β-Alkyl-cis-decahydroquinoline of Myrioneuron nutans

  摘要：

  Myrionine (1), a new 8 beta-alkyl-cis-decahydroquinoline, was isolated from Myrioneuron nutans. Its structure was determined by spectral methods and then confirmed by X-ray analysis and total synthesis. In solution, 1 gives rise to an N-in/N-out equilibrium. The solvent has weak influence on the N-in/N-out ratio for myrionine (1), whereas together with the anions, it plays an important role for myrionine hydrochloride (9) and hydroiodide (10). The two N-in and N-out conformations obtained separately by crystallization of 9 and 10, respectively, were analyzed by X-ray diffraction.

  DOI：

  10.1021/ol071393a

文献信息

• Novel Alkaloids from<i>Myrioneuron nutans</i>
  作者：Van Cuong Pham、Akino Jossang、Thierry Sévenet、Van Hung Nguyen、Bernard Bodo

  DOI：10.1002/ejoc.200801028

  日期：2009.3

  Two new alkaloids, dehydronitraramine (1) and N-formylmyrionine (2) were isolated from the leaves of Myrioneuron nutans, and their structures were determined from spectroscopic analysis, including mass spectrometry and 2D-NMR spectroscopy. The absolute configuration 8S, 9R, 10S of N-formylmyrionine (2) was established by N-formylation of the known (8S,9R,10S)-myrionine and then comparison of the optical

  从 Myrioneuron nutans 的叶子中分离出两种新的生物碱脱氢硝胺 (1) 和 N-甲酰基肉豆碱 (2)，并通过光谱分析确定了它们的结构，包括质谱和 2D-​​NMR 光谱。N-甲酰基肉豆蔻氨酸 (2) 的绝对构型 8S、9R、10S 是通过已知 (8S,9R,10S)-肉豆蔻氨酸的 N-甲酰化建立的，然后将天然 N-甲酰基肉豆蔻氨酸 (2) 的旋光度与半合成 (8S,9R,10S)-N-甲酰基肉豆氨酸。Dehydronitraramine (1) 对恶性疟原虫显示出中等的抗疟原虫活性，IC50 值为 16 μM，而 1 和 2 对 KB 细胞显示出较弱的细胞毒性。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009 )
• Structure and Total Synthesis of (−)-Myrionidine and (−)-Schoberine, Antimalarial Alkaloids from <i>Myrioneuron nutans</i>
  作者：Van Cuong Pham、Akino Jossang、Philippe Grellier、Thierry Sévenet、Van Hung Nguyen、Bernard Bodo

  DOI：10.1021/jo801046j

  日期：2008.10.3

  Two new alkaloids, (5S,9S,10R)-myrionidine (1) and (5S,9S,10R,13S)-myrionamide (2), along with the known schoberine (3), were isolated from the leaves of Myrioneuron nutans (Rubiaceae), and their structures were determined from spectral analysis, including mass spectrometry and 2D NMR. The total asymmetric syntheses of (-)-myrionidine (1), (-)-schoberine (3), their enantiomers as well as their 9-epimers

  从Myrioneuron nutan（茜草科）及其结构是通过光谱分析（包括质谱和2D NMR）确定的。进行了（-）-myrionidine（1），（-）-schoberine（3），其对映异构体以及9-epimers衍生物的总不对称合成，从而确定了其与Myrionamide（2的绝对构型）的绝对构型）。（-）-Myrionidine（1）及其合成对映异构体（18）对恶性疟原虫具有显着的抗疟活性。
• Solution and Crystal Conformations of Myrionine, a New 8β-Alkyl-<i>cis</i>-decahydroquinoline of <i>Myrioneuron nutans</i>
  作者：Van Cuong Pham、Akino Jossang、Angèle Chiaroni、Thierry Sévenet、Van Hung Nguyen、Bernard Bodo

  DOI：10.1021/ol071393a

  日期：2007.8.1

  Myrionine (1), a new 8 beta-alkyl-cis-decahydroquinoline, was isolated from Myrioneuron nutans. Its structure was determined by spectral methods and then confirmed by X-ray analysis and total synthesis. In solution, 1 gives rise to an N-in/N-out equilibrium. The solvent has weak influence on the N-in/N-out ratio for myrionine (1), whereas together with the anions, it plays an important role for myrionine hydrochloride (9) and hydroiodide (10). The two N-in and N-out conformations obtained separately by crystallization of 9 and 10, respectively, were analyzed by X-ray diffraction.