methyl 12α,13-epoxy-15a-homo-isoanticopal-15-oate | 1309883-84-8

• 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: methyl 12α,13-epoxy-15a-homo-isoanticopal-15-oate
• 英文别名: methyl 2-[(1R,2S,7S,10R,11S,12R,14S)-2,6,6,10,12-pentamethyl-13-oxatetracyclo[8.5.0.02,7.012,14]pentadecan-11-yl]acetate
• CAS: 1309883-84-8
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: JDCKNVWGXIKZDP-SIFNXDFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 12α,13-epoxy-15a-homo-isoanticopal-15-oate 在 氯化亚砜 、 palladium 10% on activated carbon 、 氢碘酸 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醚 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 40.42h， 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：

  15a-homo-isoanticopal-12-en-15-al 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 3.17h， 生成 methyl 12α,13-epoxy-15a-homo-isoanticopal-15-oate
  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 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.