N-methyl-N-[(3α)-23-(3-methylpyridin-4-yl)-24-nor-5α,22E-chola-7,22-dien-3-yl]-2-nitrobenzenesulfonamide | 1542168-62-6

• 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-methyl-N-[(3α)-23-(3-methylpyridin-4-yl)-24-nor-5α,22E-chola-7,22-dien-3-yl]-2-nitrobenzenesulfonamide
• 英文别名: N-[(3R,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(E,2R)-4-(3-methylpyridin-4-yl)but-3-en-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-N-methyl-2-nitrobenzenesulfonamide
• CAS: 1542168-62-6
• 化学式: C₃₆H₄₇N₃O₄S
• 分子量: 617.853
• InChiKey: CUOUKZRETBIHOX-MNNPYMKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-methyl-N-[(3α)-23-(3-methylpyridin-4-yl)-24-nor-5α,22E-chola-7,22-dien-3-yl]-2-nitrobenzenesulfonamide 在 sodium tetrahydroborate 、 caesium carbonate 、 苯硫酚 作用下， 以 乙醇 、 丙酮 、 乙腈 为溶剂， 反应 51.0h， 生成 (3α)-23-(1,3-dimethyl-1,2,5,6-tetrahydropyridin-4-yl)-3-methylamino-24-nor-5α,22E-chola-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：

  3,4-二甲基吡啶 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 sodium hydroxide 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 89.08h， 生成 N-methyl-N-[(3α)-23-(3-methylpyridin-4-yl)-24-nor-5α,22E-chola-7,22-dien-3-yl]-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.