(5R,10R)-6-methyl-(8R)-acetoxymethyl-ergoline | 111001-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (5R,10R)-6-methyl-(8R)-acetoxymethyl-ergoline
• 英文别名: 6-Methyl-8β-acetoxymethylergoline；8β-acetoxymethyl-6-methyl-ergoline；8β-Acetoxymethyl-6-methyl-ergolin；Methanol, [(8beta)-6-methylergolin-8-yl]-, acetate (ester)；[(6aR,9R,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl acetate
• CAS: 111001-59-3
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: PTSNJISFSNIKMW-SRCQZFHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,10R)-6-methyl-(8R)-acetoxymethyl-ergoline 在 四氯化锡 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 0.5h， 生成 (2R,3R,4R,5R)-2-((6aR,9R,10aR)-9-(acetoxymethyl)-7-methyl-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-4(6H)-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of N-β-D-Ribosides of Ergot Alkaloids

  摘要：

  N-beta-D-Ribosides of agroclavine (1), elymoclavine (2), lysergene (4), lysergol (3), and 9,10-dihydrolysergol (5) were prepared by SnCl2 catalyzed ribosylation of their TMS derivatives with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose. None of the new compounds exhibited activity against HIV or other viruses tested.

  DOI：

  10.1080/07328319708002525
• 作为产物：
  描述：

  9,10-dihydrolysergic acid methyl ester 在 吡啶 、 sodium tetrahydroborate 作用下， 生成 (5R,10R)-6-methyl-(8R)-acetoxymethyl-ergoline
  参考文献：
  名称：

  Diastereospecific formation of 6-N-oxide ergolines: a 1H NMR study of the configuration at nitrogen

  摘要：

  The 6-N-oxides derivatives of a series of analogous ergoline/ene derivatives were prepared and their stereochemistry at nitrogen determined by H-1 NMR analysis. The factors governing the outcome of the oxidation are discussed.

  DOI：

  10.1016/s0040-4020(01)81229-1

文献信息

• N-1-Trimethylsilyl Derivatives of Ergot Alkaloids
  作者：Vladimír Křen、Petr Sedmera

  DOI：10.1135/cccc19961248

  日期：——

  N-1-Trimethylsilyl derivatives of five different suitably protected parent ergot (clavine) alkaloids (agroclavine 1a, elymoclavine 2a, lysergol 3a, lysergene 4a, and 9,10-dihydrolysergol 5a) were prepared in 47-94% yields by refluxing the (protected) parent compounds with N-methyl-N-(trimethylsilyl)trifluoroacetamide in acetonitrile under nitrogen atmosphere.

  五种不同的适当保护的母麦角生物碱（农业麦角碱1a，艾利莫麦角碱2a，利塞尔醇3a，利塞尔基因4a和9,10-二氢利塞尔醇5a）的N-1-三甲基硅基衍生物以47-94%的产率通过在氮气氛下用乙腈回流（受保护的）母化合物与N-甲基-N-（三甲基硅基）三氟乙酰胺制备。
• Electrochemical Synthesis of 2-Haloergolines
  作者：Giovanni Palmisano、Bruno Danieli、Giordano Lesma、Giorgio Fiori

  DOI：10.1055/s-1987-27862

  日期：——

  Regioselective halogenation (chlorination, bromination, iodination) of several ergolines to the corresponding 2-halo derivatives was performed in moderate to good yields by potential controlled electrolysis at platinum in acetonitrile in the presence of tetrabutylammonium halide and lithium perchlorate. Alternatively, ergolines underwent a facile iodination in excellent yields by exposure to an anodically oxidized solution of iodine in acetonitrile.

  在四丁基卤化铵和高氯酸锂的存在下，通过在乙腈中在铂上进行电位控制电解，对几种麦角林进行了区域选择性卤化（氯化、溴化、碘化），生成了相应的 2-卤衍生物，收率为中等到良好。另外，将麦角林暴露于乙腈中碘的阳极氧化溶液中，也能以极好的收率进行简单的碘化反应。
• N -Deoxyribosides of ergot alkaloids: Synthesis and biological activity
  作者：Vladimír Křen、Petr Olšovský、Vladimír Havlíček、Petr Sedmera、Myriam Witvrouw、Erik De Clecq

  DOI：10.1016/s0040-4020(97)00123-3

  日期：1997.3

  N-Deoxyribosides of agroclavine (1), lysergol (2), and 9,10-dihydrolysergol (3) were prepared by SnCl4-catalyzed N-glycosylation of their TMS derivatives with 1-chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose. None of the new compounds exhibited activity against HIV. (C) 1997 Elsevier Science Ltd.
• Studies on oxidation of ergot alkaloids: oxidation and desaturation of dihydrolysergol—stereochemical requirements
  作者：Radek Gažák、Vladimír Křen、Petr Sedmera、Daniele Passarella、Michaela Novotná、Bruno Danieli

  DOI：10.1016/j.tet.2007.07.099

  日期：2007.10

  A new method for the oxidation of ergoline alcohols to aldehydes was found (TFFA-DMSO, -78 degrees C, then DIPEA). Structural features of ergolines required for successful C7-C8 double bond introduction via Polonovski-Potier reaction of respective 6-N-oxides were defined and experimentally confirmed: (i) the presence of electron-withdrawing group at C-8; (ii) trans-diaxial orientation of N6-O and C7-H bonds ( both requirements are fulfilled for dihydrolyserg-17-al and its 2,4-dinitrophenyl hydrazone prepared in this work). (c) 2007 Published by Elsevier Ltd.
• PALMISANO, GIOVANNI;BRENNA, ELISABETTA;DANIELI, BRUNO;LESMA, GIORDANO;VOD+, TETRAHEDRON LETT., 31,(1990) N9, C. 7229-7232
  作者：PALMISANO, GIOVANNI、BRENNA, ELISABETTA、DANIELI, BRUNO、LESMA, GIORDANO、VOD+

  DOI：——

  日期：——