(S)-dihydroxyverbacine | 312908-82-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (S)-dihydroxyverbacine
• 英文别名: (8S)-8-(4-hydroxyphenyl)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-1,5,9,13-tetrazacycloheptadecan-6-one
• CAS: 312908-82-0
• 化学式: C₂₈H₃₈N₄O₄
• 分子量: 494.634
• InChiKey: ABGQXMKZCQIDRG-FESLSTPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  114
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-dihydroxyverbacine 在 soluble protein fraction of barley seedlings 作用下， 以 phosphate buffer 为溶剂， 反应 1.0h， 以25%的产率得到(3S,3aS,15S)-3,3a,6,7,8,9,10,11,12,13,14,15-十二氢-3-(4-羟基苯基)-4H-1,16-乙烯桥-5,15-(丙亚氨基乙桥)呋喃并[3,4-l][1,5,10]三氮杂环十六烷-4,21-二酮
  参考文献：
  名称：

  New reagent for oxidative phenol coupling. The transformation of the monocyclic spermine base (S)-dihydroxyverbacine to the bicyclic alkaloid (S,S,S)-aphelandrine by cell free extract of barley seedlings

  摘要：

  The soluble protein fraction of barley seedlings (Hordeum vulgare, Gramineae) in the presence of O-2 stereoselectively catalyzes the intramolecular phenol coupling of the monocyclic spermine base (S)-dihydroxyverbacine to the bicyclic aphelandrine in preparative yield. The expected microsomal-bond cytochrome P-450 enzyme system does not contribute to this reaction. The nature of the involved biocatalyst still remains uncertain. The catalytic potential of the cell free extract of barley seedlings suggests its possible use as an efficient tool for large scale stereoselective chemoenzymatic synthesis of aphelandrine type alkaloids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00670-0
• 作为产物：
  描述：

  (-)-(S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 在 聚合甲醛 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-dihydroxyverbacine
  参考文献：
  名称：

  Biomimetic Formation of Macrocyclic Spermine Alkaloids

  摘要：

  Dihydroxyverbacine (10), a precursor for oxidative phenol coupling. was obtained via (+/-)-buchnerine (14). whose synthesis is described. The oxidizing system hemin (ferriprotoporphyrin IX chloride)/H2O2 promoted intramolecular coupling of 10 to give the alkaloids aphelandrine (1). orantine (2), and chaenorpine (7). The alkaloids were identified by on-line coupled HPLC and atmospheric-pressure chemical-ionization (APCI) mass spectrometry.

  DOI：

  10.1002/1522-2675(20010711)84:7<2108::aid-hlca2108>3.0.co;2-g

文献信息

• Biomimetic Formation of Macrocyclic Spermine Alkaloids
  作者：Vladimir Dimitrov、Hervé Geneste、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/1522-2675(20010711)84:7<2108::aid-hlca2108>3.0.co;2-g

  日期：2001.7.11

  Dihydroxyverbacine (10), a precursor for oxidative phenol coupling. was obtained via (+/-)-buchnerine (14). whose synthesis is described. The oxidizing system hemin (ferriprotoporphyrin IX chloride)/H2O2 promoted intramolecular coupling of 10 to give the alkaloids aphelandrine (1). orantine (2), and chaenorpine (7). The alkaloids were identified by on-line coupled HPLC and atmospheric-pressure chemical-ionization (APCI) mass spectrometry.
• New reagent for oxidative phenol coupling. The transformation of the monocyclic spermine base (S)-dihydroxyverbacine to the bicyclic alkaloid (S,S,S)-aphelandrine by cell free extract of barley seedlings
  作者：Lenka Nezbedová、Manfred Hesse、Konstantin Drandarov、Christa Werner

  DOI：10.1016/s0040-4039(01)00670-0

  日期：2001.6

  The soluble protein fraction of barley seedlings (Hordeum vulgare, Gramineae) in the presence of O-2 stereoselectively catalyzes the intramolecular phenol coupling of the monocyclic spermine base (S)-dihydroxyverbacine to the bicyclic aphelandrine in preparative yield. The expected microsomal-bond cytochrome P-450 enzyme system does not contribute to this reaction. The nature of the involved biocatalyst still remains uncertain. The catalytic potential of the cell free extract of barley seedlings suggests its possible use as an efficient tool for large scale stereoselective chemoenzymatic synthesis of aphelandrine type alkaloids. (C) 2001 Elsevier Science Ltd. All rights reserved.