'dioncolactone A' | 135626-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 'dioncolactone A'
• 英文别名: (16R,18R)-7-hydroxy-9-methoxy-16,18-dimethyl-13-oxa-17-azapentacyclo[12.8.0.02,11.03,8.015,20]docosa-1(14),2,4,6,8,10,15(20),21-octaen-12-one
• CAS: 135626-75-4
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: JXIICUPAPXXMPH-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  'dioncolactone A' 在 lithium aluminium tetrahydride 、 甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 N-formyl-dioncopeltine A
  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：

  (1R,3R)-2-Benzyl-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-8-ol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 草酰氯 、 氢气 、 sodium acetate 、 三氯化硼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 10.33h， 生成 'dioncolactone A'
  参考文献：
  名称：

  三个naphthylisoquinoline生物碱涉及关节的总合成dioncolactone A，dioncopeltine A，和5'- Ò -demethyldioncophylline甲

  摘要：

  的第一全合成三个抗疟疾naphthylisoquinoline生物碱dioncolactone A（4），dioncopeltine A（5），和5'- Ô -demethyldioncophylline A（6）进行说明。通过“内酯法”，通过两个分子部分的酯型前缀，分子内偶联和内酯辅助桥的对苯二酸-非对映选择性裂解，实现了芳基轴的区域和立体选择性构建。作为一种新颖的替代方案，可以通过动态动力学拆分通过对映选择性羟基醛还原来安装在轴上的构型。

  DOI：

  10.1016/s0040-4020(98)01040-0

文献信息

• Directed joint total synthesis of the three naphthylisoquinoline alkaloids dioncolactone A, dioncopeltine A, and 5′-O-demethyldioncophylline A
  作者：Gerhard Bringmann、Wael Saeb、Martin Rübenacker

  DOI：10.1016/s0040-4020(98)01040-0

  日期：1999.1

  described. The regio- and stereo-selective construction of the biaryl axes was achieved through the ‘lactone methodology’, by ester-type prefixation of the two molecular moieties, intramolecular coupling, and atropo-diastereoselective cleavage of the lactone auxiliary bridge. As a novel alternative, the configuration at the axis may be installed by atroposelective hydroxy aldehyde reduction through dynamic

  的第一全合成三个抗疟疾naphthylisoquinoline生物碱dioncolactone A（4），dioncopeltine A（5），和5'- Ô -demethyldioncophylline A（6）进行说明。通过“内酯法”，通过两个分子部分的酯型前缀，分子内偶联和内酯辅助桥的对苯二酸-非对映选择性裂解，实现了芳基轴的区域和立体选择性构建。作为一种新颖的替代方案，可以通过动态动力学拆分通过对映选择性羟基醛还原来安装在轴上的构型。
• 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.