alstonerinal | 158725-12-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 大灵碱生物碱
• 英文名称: alstonerinal
• 英文别名: Alstonerinal；(1S,12S,13R,18R)-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8,16-pentaene-17-carbaldehyde
• CAS: 158725-12-3
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: AUSQYXZCCIDHMV-KTGNWYGMSA-N

物化性质

• 沸点：
  511.9±50.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  alstonerinal 在 sodium tetrahydroborate 、 alstonerine 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以6 mg的产率得到
  参考文献：
  名称：

  Alkaloids from the stem-bark of Alstonia macrophylla

  摘要：

  Three new indole alkaloids, viz. 10-methoxyaffinisine, 10-methoxycathafoline and alstonerinal, in addition to alstonerine, alstonisine, alstonal, alstophylline, vincamajine, lochnerine and cathafoline were isolated from the stem-bark extract of Alstonia macrophylla. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00044-8
• 作为产物：
  描述：

  (6S,10S)-(-)-5,12-dimethyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 三正丁基氧化磷 、 双氧水 、 lithium perchlorate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 116.0h， 生成 alstonerinal
  参考文献：
  名称：

  Enantiospecific Synthesis of (-)-Alstonerine and (+)-Macroline as Well as a Partial Synthesis of (+)-Villalstonine

  摘要：

  The enantiospecific synthesis of (-)-alstonerine (5) and (+)-macroline (8), as well as a partial synthesis of the Alstonia bisindole alkaloid villalstonine (2) has been completed. In addition, a more stable macroline equivalent 9 was prepared. The stereochemistry at C(15) and C(16) in 5 and 8 has been successfully installed by a stereoselective Claisen rearrangement followed by stereospecific hydroboration-oxidation of the exocyclic methylene function at C-16. The E ring in alstonerine 5 was constructed by a regioselective cyclization followed by a novel Swern oxidation under modified conditions [(COCl)(2)/DMSO/CH2Cl2, -78 degrees C to -10 degrees C/1.5 h; Et(3)N], whereas the C(20)-C(21) enone system in macroline (8) was generated via a convenient one pot process from the beta-diol 45. Condensation of either synthetic (+)-macroline (8) or the macroline equivalent 9 with natural pleiocarpamine 7 in 0.2 N HCl furnished the antiamoebic, antimalarial bisindole alkaloid villalstonine 2. This constitutes the first partial synthesis of any of the Alstonia bisindoles from a synthetically derived indole moiety.

  DOI：

  10.1021/ja00099a021
• 作为试剂：
  描述：

  alstonerine 在 sodium tetrahydroborate 、 alstonerinal 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以22 mg的产率得到1-((4aR,6S,13S,13aR)-7,14-dimethyl-1,4a,5,6,7,12,13,13a-octahydro-6,13-epiminopyrano[3',4':5,6]cycloocta[1,2-b]indol-4-yl)ethan-1-ol
  参考文献：
  名称：

  Alkaloids from the stem-bark of Alstonia macrophylla

  摘要：

  Three new indole alkaloids, viz. 10-methoxyaffinisine, 10-methoxycathafoline and alstonerinal, in addition to alstonerine, alstonisine, alstonal, alstophylline, vincamajine, lochnerine and cathafoline were isolated from the stem-bark extract of Alstonia macrophylla. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00044-8

文献信息

• Enantiospecific Synthesis of (-)-Alstonerine and (+)-Macroline as Well as a Partial Synthesis of (+)-Villalstonine
  作者：Yingzhi Bi、Lin-Hua Zhang、Linda K. Hamaker、James M. Cook

  DOI：10.1021/ja00099a021

  日期：1994.10

  The enantiospecific synthesis of (-)-alstonerine (5) and (+)-macroline (8), as well as a partial synthesis of the Alstonia bisindole alkaloid villalstonine (2) has been completed. In addition, a more stable macroline equivalent 9 was prepared. The stereochemistry at C(15) and C(16) in 5 and 8 has been successfully installed by a stereoselective Claisen rearrangement followed by stereospecific hydroboration-oxidation of the exocyclic methylene function at C-16. The E ring in alstonerine 5 was constructed by a regioselective cyclization followed by a novel Swern oxidation under modified conditions [(COCl)(2)/DMSO/CH2Cl2, -78 degrees C to -10 degrees C/1.5 h; Et(3)N], whereas the C(20)-C(21) enone system in macroline (8) was generated via a convenient one pot process from the beta-diol 45. Condensation of either synthetic (+)-macroline (8) or the macroline equivalent 9 with natural pleiocarpamine 7 in 0.2 N HCl furnished the antiamoebic, antimalarial bisindole alkaloid villalstonine 2. This constitutes the first partial synthesis of any of the Alstonia bisindoles from a synthetically derived indole moiety.
• Alkaloids from the stem-bark of Alstonia macrophylla
  作者：Toh-Seok Kam、Ing-Ho Iek、Yeun-Mun Choo

  DOI：10.1016/s0031-9422(99)00044-8

  日期：1999.7

  Three new indole alkaloids, viz. 10-methoxyaffinisine, 10-methoxycathafoline and alstonerinal, in addition to alstonerine, alstonisine, alstonal, alstophylline, vincamajine, lochnerine and cathafoline were isolated from the stem-bark extract of Alstonia macrophylla. (C) 1999 Elsevier Science Ltd. All rights reserved.