[(8R,9R,10S)-N-benzyl-decahydroquinolin-8-yl]methanol | 951681-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [(8R,9R,10S)-N-benzyl-decahydroquinolin-8-yl]methanol
• 英文别名: [(5S,9R,10R)-N-benzyl-decahydroqinolin-9-yl]methanol；[(4aS,8R,8aR)-1-benzyl-3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-8-yl]methanol
• CAS: 951681-64-4
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: OASARJMZAAEGAN-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(8R,9R,10S)-N-benzyl-decahydroquinolin-8-yl]methanol 在 palladium on activated charcoal 氢气 、 potassium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 4.0h， 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
• 作为产物：
  描述：

  溴甲苯 、 (4 aS,8R,8aR)-8-(hydroxymethyl)decahydroquinoline 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以93%的产率得到[(8R,9R,10S)-N-benzyl-decahydroquinolin-8-yl]methanol
  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

文献信息

• 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.