N-formyl-8-O-methyldioncophylline A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-formyl-8-O-methyldioncophylline A
• 英文别名: (1R,3R)-7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,3-dimethyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde
• 化学式: C₂₆H₂₉NO₄
• 分子量: 419.521
• InChiKey: KTGGQZQECBZHDA-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-formyl-8-O-methyldioncophylline A 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 8-O-methyl-dioncophylline A hydrochloride
  参考文献：
  名称：

  Dioncopeltine A and dioncolactone A: Alkaloids from Triphyophyllum peltatum

  摘要：

  The isolation of two novel alkaloids from Triphyophyllum peltatum is described. The complete stereostructure of dioncopeltine A, which is closely related to dioncophylline A, is established by spectroscopic, chiroptical, and degradative methods, and is furthermore confirmed by its transformation to O-methyl-dioncopophylline A, as well as by X-ray crystallography. Dioncolactone A, which can be transformed into dioncopeltine A by reductive ring-opening, is the first naturally occurring representative of this novel type of 'axially prostereogenic' biaryl alkaloids.

  DOI：

  10.1016/0031-9422(91)84235-k
• 作为产物：
  描述：

  dioncophylline A 在 氢氧化钾 、 苄基三丁基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-formyl-8-O-methyldioncophylline A
  参考文献：
  名称：

  5′-O-demethyl-8-O-methyl-7-epi-dioncophylline a and its ‘regularly’ configurated atropisomer from Triphyophyllum peltatum

  摘要：

  The isolation and structure elucidation of two new minor naphthylisoquinoline alkaloids from the stem bark of Triphyophyllum peltatum is described. From extended spectroscopic investigations, mainly NMR and CD spectroscopy, one of the alkaloids is deduced to be 5'-O-demethyl-8-O-methyl-7-epi-dioncophylline A. This new natural product is, thus, the first dioncophylline A analogous naphthylisoquinoline alkaloid from T. peltatum with an opposite configuration at the biaryl axis. Moreover, low amounts of an additional new alkaloid were isolated, whose spectral data suggest 5'-O-demethyl-8-O-methyl-dioncophylline A, i.e. the corresponding 'normal' atropodiastereomer.

  DOI：

  10.1016/s0031-9422(00)90491-6

文献信息

• BRINGMANN, GERHARD;RUBENACKER, MARTIN;VOGT, PETER;BUSSE, HOLGER;AKE, ASSI+, PHYTOCHEMISTRY, 30,(1991) N, C. 1691-1696
  作者：BRINGMANN, GERHARD、RUBENACKER, MARTIN、VOGT, PETER、BUSSE, HOLGER、AKE, ASSI+

  DOI：——

  日期：——
• 5′-O-demethyl-8-O-methyl-7-epi-dioncophylline a and its ‘regularly’ configurated atropisomer from Triphyophyllum peltatum
  作者：Gerhard Bringmann、Martin Rübenacker、Wolfgang Koch、Dagmar Koppler、Thomas Ortmann、Manuela Schäffer、Laurent Aké Assi

  DOI：10.1016/s0031-9422(00)90491-6

  日期：1994.7

  The isolation and structure elucidation of two new minor naphthylisoquinoline alkaloids from the stem bark of Triphyophyllum peltatum is described. From extended spectroscopic investigations, mainly NMR and CD spectroscopy, one of the alkaloids is deduced to be 5'-O-demethyl-8-O-methyl-7-epi-dioncophylline A. This new natural product is, thus, the first dioncophylline A analogous naphthylisoquinoline alkaloid from T. peltatum with an opposite configuration at the biaryl axis. Moreover, low amounts of an additional new alkaloid were isolated, whose spectral data suggest 5'-O-demethyl-8-O-methyl-dioncophylline A, i.e. the corresponding 'normal' atropodiastereomer.
• Dioncopeltine A and dioncolactone A: Alkaloids from Triphyophyllum peltatum
  作者：Gerhard Bringmann、Martin Rübenacker、Peter Vogt、Holger Busse、Laurent Aké Assi、Karl Peters、Hans Georg von Schnering

  DOI：10.1016/0031-9422(91)84235-k

  日期：1991.1

  The isolation of two novel alkaloids from Triphyophyllum peltatum is described. The complete stereostructure of dioncopeltine A, which is closely related to dioncophylline A, is established by spectroscopic, chiroptical, and degradative methods, and is furthermore confirmed by its transformation to O-methyl-dioncopophylline A, as well as by X-ray crystallography. Dioncolactone A, which can be transformed into dioncopeltine A by reductive ring-opening, is the first naturally occurring representative of this novel type of 'axially prostereogenic' biaryl alkaloids.