reticulatin A | 1449432-45-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: reticulatin A
• 英文别名: (2S)-3-(1,3-dimethyl-5-methylsulfanylimidazol-1-ium-4-yl)-2-hydroxypropanoate
• CAS: 1449432-45-4
• 化学式: C₉H₁₄N₂O₃S
• 分子量: 230.288
• InChiKey: DIJZRURIOWLBFY-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  reticulatin A 、 甲基2-(苯基氨基)乙酸酯 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Reticulatins A and B and hyrtioreticulin F from the marine sponge Hyrtios reticulatus

  摘要：

  Three new alkaloids, reticulatins A (1) and B (2) and hyrtioreticulin F (3), were isolated from the water-soluble fraction of an EtOH extract of the marine sponge Hyrtios reticulatus. Compounds 1 and 2 were found to be novel 1,3-dimethyl-5-(methylthio)imidazolium alkaloids. The structure of 3 was determined to be an indole alkaloid related to hyrtioreticulin E (8) and hyrtioerectine B (9), which were isolated previously from the n-BuOH-soluble fraction of the sponge extract. The presence of three NH units in 3 was indicated by the H-1-N-15 HSQC spectrum in D2O/H2O (5:95) containing 0.05% TFA measured at 5 degrees C. Compound 3 is likely biosynthesized from L-tryptophan, two units of L-alanine, and glycine by the Pictet-Spengler reaction. The absolute configurations of 1-3 were determined by the methods based on ECD spectra. In addition, the result for 1 was further confirmed by the PGME method. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.043