spongida-13(21),14,16-triene | 1309883-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: spongida-13(21),14,16-triene
• 英文别名: (4bR,6aS,10aS,10bR)-4b,7,7,10a-tetramethyl-6,6a,8,9,10,10b,11,12-octahydro-5H-naphtho[2,1-f]isoquinoline
• CAS: 1309883-79-1
• 化学式: C₂₁H₃₁N
• 分子量: 297.484
• InChiKey: AGWOTSMYDUIBSK-QIJZPMMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  spongida-13(21),14,16-triene 以 甲醇 、 乙醚 、 C₆H₅Br 、 苯 为溶剂， 反应 24.25h， 生成 methyl spongidine A
  参考文献：
  名称：

  Synthesis of spongidines A and D: marine metabolites phospholipase A2 inhibitors

  摘要：

  Two different strategies for the synthesis of spongidines A and D are presented. Herein we describe a route based in an amino acid insertion followed by aromatization. Another alternative is the construction of a pyridine derivative followed by N-alkylation. Both methodologies have intermediate 5 as a key compound, which is eventually accessible from methyl isoanticopalate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.084
• 作为产物：
  描述：

  spongida-13(21),14,16-trien-16-yl trifluoromethanesulfonate 在 1,1'-双(二苯基膦)二茂铁 、 甲酸铵 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以67%的产率得到spongida-13(21),14,16-triene
  参考文献：
  名称：

  Synthesis of spongidines A and D: marine metabolites phospholipase A2 inhibitors

  摘要：

  Two different strategies for the synthesis of spongidines A and D are presented. Herein we describe a route based in an amino acid insertion followed by aromatization. Another alternative is the construction of a pyridine derivative followed by N-alkylation. Both methodologies have intermediate 5 as a key compound, which is eventually accessible from methyl isoanticopalate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.084

文献信息

• Synthesis of Spongidine A and D and Petrosaspongiolide L Methyl Ester Using Pyridine C–H Functionalization
  作者：Florian Bartels、Manuela Weber、Mathias Christmann

  DOI：10.1021/acs.orglett.9b04315

  日期：2020.1.17

  strategy for the synthesis of the potent phospholipase A2 inhibitors spongidine A and D is presented. The tetracyclic core of the natural products was assembled via an intramolecular hydrogen atom transfer initiated Minisci reaction. A divergent late-stage functionalization of the tetracyclic ring system was also used to achieve a concise synthesis of petrosaspongiolide L methyl ester.

  提出了一种有效的合成有效的磷脂酶A2抑制剂海绵丁A和D的策略。天然产物的四环核是通过分子内氢原子转移引发的Minisci反应组装的。四环体系的后期官能化的发散性也用于实现简并合成石油醚双糖脂内酯L甲酯。
• Synthesis of spongidines A and D: marine metabolites phospholipase A2 inhibitors
  作者：P. Basabe、A. Blanco、I.S. Marcos、D. Díez、O. Bodero、M. Martín、J.G. Urones

  DOI：10.1016/j.tet.2011.03.084

  日期：2011.5

  Two different strategies for the synthesis of spongidines A and D are presented. Herein we describe a route based in an amino acid insertion followed by aromatization. Another alternative is the construction of a pyridine derivative followed by N-alkylation. Both methodologies have intermediate 5 as a key compound, which is eventually accessible from methyl isoanticopalate. (C) 2011 Elsevier Ltd. All rights reserved.