androst-5-en-17-on-3β-yl isonicotinate

• 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: androst-5-en-17-on-3β-yl isonicotinate
• 英文别名: (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl isonicotinate；[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] pyridine-4-carboxylate
• 化学式: C₂₅H₃₁NO₃
• 分子量: 393.526
• InChiKey: MJGRKPJFTDKUAD-FYVXYBBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  androst-5-en-17-on-3β-yl isonicotinate 、 methyl-2-diazo-2-(2-((3-phenylprop-2-yn-1-yl)oxy)phenyl)acetate 在 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以63%的产率得到(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 7-phenyl-6H-chromeno[3,4-b]indolizine-9-carboxylate
  参考文献：
  名称：

  铜催化的由炔烃连接的重氮乙酸盐和吡啶的正式[1 + 2 + 2]环化反应：可得到多环吲哚嗪。

  摘要：

  据报导，铜连接的炔烃系重氮化合物与吡啶的正式[1 + 2 + 2]环化反应，可在温和的反应条件下提供多环稠合的吲哚并嗪，可合成用于高产。该方法的特点是使用廉价的铜催化剂和易于获得的起始原料，广泛的底物通用性和操作简便性。值得注意的是，多种天然产物衍生物在当前条件下是相容的，这表明该方法用于选择性修饰和修饰类似生物分子或药物的巨大潜力。

  DOI：

  10.1039/d0ob00222d
• 作为产物：
  描述：

  异烟酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 androst-5-en-17-on-3β-yl isonicotinate
  参考文献：
  名称：

  Synthesis of pyridine-carboxylate derivatives of hydroxysteroids for liquid chromatography–electrospray ionization-mass spectrometry

  摘要：

  Synthesis and liquid chromatography-electrospray ionization-mass spectrometric (LC-ESI-MS) behaviors of the picolinoyl, 6-methylpicolinoyl, nicotinoyl, 2-methoxynicotinoyl and isonicotinoyl derivatives of the hydroxysteroids estrone, estradiol, 3 beta-hydroxyandrost-5en-17-one (dehydroepiandrosterone) and testosterone in positive mode were investigated. Each steroid was converted to the corresponding pyridine-carboxylate derivative by the acyl chloride method or the mixed anhydride method using the corresponding free acids and 2-methyl-6-nitrobenzoic anhydride; in each case, the latter method principally gave a better yield. The pyridine-carboxylate derivative of each steroid exhibited a clear single peak in liquid chromatography with a reversed phase column and CH3CN-0.1% CH3COOH as a mobile phase. The positive-ESI-mass spectra of the picolinoyl, 6-methylpicolinoyl and 2-methoxynicotinoyl derivatives showed a predominance of [M+H](+), whereas [M+H+CH3CN](+) was observed with high intensity in the nicotinoyl and isonicotinoyl derivatives. Even in the case of estradiol, with its two hydroxyl groups, a single charged ion of [M+H](+) or [M+H+CH3CN](+) was observed in the positive-ESI-mass spectrum of each derivative. The results revealed that picolinoyl derivatization is a simple and versatile method suitable for the sensitive and specific determination of hydroxysteroids by LC-ESI-MS (selected reaction monitoring). (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.10.005