3α-(N-Methylamino)-5α-ergosta-7,22-diene | 93474-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3α-(N-Methylamino)-5α-ergosta-7,22-diene
• 英文别名: (3α)-methylaminoergosta-7,22E-diene；(3R,5S,9R,10S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-N,10,13-trimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine
• CAS: 93474-19-2
• 化学式: C₂₉H₄₉N
• 分子量: 411.715
• InChiKey: KGOHWUCDOBGHCJ-FDMDADQNSA-N

物化性质

• 沸点：
  488.1±44.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  星鱼甾醇 在 caesium carbonate 、 苯硫酚 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 15.0h， 生成 3α-(N-Methylamino)-5α-ergosta-7,22-diene
  参考文献：
  名称：

  First total synthesis of the marine steroid alkaloid plakinamine B

  摘要：

  The first total synthesis of the marine steroid alkaloid plakinamine B (1) was accomplished in seven steps starting from known aldehyde 3. Key steps in this synthesis are the attachment of a vinylpyridine side chain by an aldol reaction, a chemoselective reduction of a pyridinium salt to a vinyl tetrahydropyridine, and the introduction of the 3 alpha-methylamino group under Mitsunobu conditions. Plakinamine B and some of its precursors with amino or pyridinium side chains show significant antimicrobial activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.065

文献信息

• Two steroidal alkaloids from a marine sponge, Plakina sp
  作者：Richard M. Rosser、D. John Faulkner

  DOI：10.1021/jo00200a029

  日期：1984.12
• First total synthesis of the marine steroid alkaloid plakinamine B
  作者：Markus Gans、Franz Bracher

  DOI：10.1016/j.tet.2013.11.065

  日期：2014.2

  The first total synthesis of the marine steroid alkaloid plakinamine B (1) was accomplished in seven steps starting from known aldehyde 3. Key steps in this synthesis are the attachment of a vinylpyridine side chain by an aldol reaction, a chemoselective reduction of a pyridinium salt to a vinyl tetrahydropyridine, and the introduction of the 3 alpha-methylamino group under Mitsunobu conditions. Plakinamine B and some of its precursors with amino or pyridinium side chains show significant antimicrobial activities. (C) 2013 Elsevier Ltd. All rights reserved.