N-[(3α)-ergosta-7,22E-dien-3-yl]-N-methyl-2-nitrobenzenesulfonamide | 1542168-60-4

• 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: N-[(3α)-ergosta-7,22E-dien-3-yl]-N-methyl-2-nitrobenzenesulfonamide
• 英文别名: N-[(3R,5S,9R,10S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-N-methyl-2-nitrobenzenesulfonamide
• CAS: 1542168-60-4
• 化学式: C₃₅H₅₂N₂O₄S
• 分子量: 596.875
• InChiKey: BIJIMQJHWMFOAT-DJFXPWMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(3α)-ergosta-7,22E-dien-3-yl]-N-methyl-2-nitrobenzenesulfonamide 在 caesium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以79%的产率得到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
• 作为产物：
  描述：

  N-甲基-2-硝基苯磺酰胺 、 星鱼甾醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以53%的产率得到N-[(3α)-ergosta-7,22E-dien-3-yl]-N-methyl-2-nitrobenzenesulfonamide
  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

• 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.