(4 aS,8R,8aR)-8-(hydroxymethyl)decahydroquinoline | 477935-36-7

• 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: (4 aS,8R,8aR)-8-(hydroxymethyl)decahydroquinoline
• 英文别名: (5S,9R,10R)-decahydroqinolin-9-ylmethanol；[(4aS,8R,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydroquinolin-8-yl]methanol
• CAS: 477935-36-7
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: DAOPHUPRXLECBY-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4 aS,8R,8aR)-8-(hydroxymethyl)decahydroquinoline 在 potassium hydride 、 sodium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 1-{[(8S,9R,10S)-N-benzyl-decahydroquinolin-8-yl]methyl}piperidin-2-one
  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：

  5,6,7,8-四氢喹啉 在 platinum(IV) oxide 吡啶 、 sodium hydroxide 、 氢气 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 65.0h， 生成 (4 aS,8R,8aR)-8-(hydroxymethyl)decahydroquinoline
  参考文献：
  名称：

  Myrioneuron nutans的新型生物碱Myrioxazines A和B的不对称合成

  摘要：

  从Myrioneuron nutans的叶子中分离出两种新的表观三环生物碱，myrioxazines A和B，并通过光谱分析（质谱和2D NMR）阐明了它们的结构。绝对构型由总不对称合成确定。

  DOI：

  10.1016/s0040-4039(02)01771-9

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。
• Enantio- and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure<i>cis</i>-Decahydroquinolines
  作者：Mercedes Amat、Elena Ghirardi、Laura Navío、Rosa Griera、Núria Llor、Elies Molins、Joan Bosch

  DOI：10.1002/chem.201302894

  日期：2013.11.18

  by the cyclocondensation of (R)‐phenylglycinol or (1S,2R)‐1‐amino‐2‐indanol with stereoisomeric mixtures (racemates, meso forms, diastereoisomers) of cyclohexanone‐based δ‐keto‐acid and δ‐keto‐diacid derivatives in enantio‐ and diastereoconvergent processes that involve dynamic kinetic resolution and/or desymmetrization of enantiotopic groups. A detailed analysis of the stereochemical outcome of this

  多达四个立构具有良好定义的配置在一个单一的合成步骤中通过（的环化缩合生成ř）-phenylglycinol或（1小号，2 - [R）-1-氨基-2-茚满醇有立体异构体混合物（外消旋体，内消旋形式对映体和非对映体聚合过程中涉及动态动力学拆分和/或对映体基团去对称化的环己酮基δ-酮酸和δ-酮-二酸衍生物。提出了对该过程的立体化学结果的详细分析。此方法可轻松获得对映纯的8和6,8-取代的顺式十氢喹啉，包括myrioxazine家族的生物碱。
• Asymmetric synthesis of myrioxazines A and B, novel alkaloids of Myrioneuron nutans
  作者：Van Cuong Pham、Akino Jossang、Angèle Chiaroni、Thierry Sévenet、Bernard Bodo

  DOI：10.1016/s0040-4039(02)01771-9

  日期：2002.10

  Two new epimeric tricyclic alkaloids, myrioxazines A and B were isolated from the leaves of Myrioneuron nutans and their structures elucidated by spectral analysis (mass spectrometry and 2D NMR). Absolute configurations were determined by total asymmetric synthesis.

  从Myrioneuron nutans的叶子中分离出两种新的表观三环生物碱，myrioxazines A和B，并通过光谱分析（质谱和2D NMR）阐明了它们的结构。绝对构型由总不对称合成确定。
• 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.