(R,4E,6E)-8-((S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-ylamino)-3,5-dimethyl-8-oxoocta-4,6-dienoic acid: | 816431-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,4E,6E)-8-((S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-ylamino)-3,5-dimethyl-8-oxoocta-4,6-dienoic acid:
• 英文别名: (1'S,3R)-farinosone C；(3R,4E,6E)-8-[[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]amino]-3,5-dimethyl-8-oxoocta-4,6-dienoic acid
• CAS: 816431-98-8
• 化学式: C₁₉H₂₅NO₅
• 分子量: 347.411
• InChiKey: PWIPPVISROQJBU-IXOAKNKVSA-N

物化性质

• 沸点：
  666.3±55.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(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：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 (R,4E,6E)-8-((S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-ylamino)-3,5-dimethyl-8-oxoocta-4,6-dienoic acid: 在 三氟乙酸 作用下， 以99%的产率得到(R,4E,6E)-methyl-8-((S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-ylamino)-3,5-dimethyl-8-oxoocta4,6-dienoate
  参考文献：
  名称：

  Total Synthesis and Neuritotrophic Activity of Farinosone C and Derivatives

  摘要：

  An efficient synthesis of all four possible stereoisomers of the neurotrophic amide farinosone C was developed. The absolute and relative configuration was assigned by comparison of synthetic material with a derivatized authentic sample of the natural product. Several derivatives allowed for the generation of preliminary structure activity relationships concerning neurite outgrowth in PC-12 cells, unravelling L-tyrosinol-amide as the pharmacophore.

  DOI：

  10.1021/ol901277q
• 作为产物：
  描述：

  tert-butyl (R,4E,6E)-8-((S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-ylamino)-3,5-dimethyl-8-oxoocta-4,6-dienoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以95%的产率得到(R,4E,6E)-8-((S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-ylamino)-3,5-dimethyl-8-oxoocta-4,6-dienoic acid:
  参考文献：
  名称：

  Total Synthesis and Neuritotrophic Activity of Farinosone C and Derivatives

  摘要：

  An efficient synthesis of all four possible stereoisomers of the neurotrophic amide farinosone C was developed. The absolute and relative configuration was assigned by comparison of synthetic material with a derivatized authentic sample of the natural product. Several derivatives allowed for the generation of preliminary structure activity relationships concerning neurite outgrowth in PC-12 cells, unravelling L-tyrosinol-amide as the pharmacophore.

  DOI：

  10.1021/ol901277q

文献信息

• Total Synthesis and Neuritotrophic Activity of Farinosone C and Derivatives
  作者：Henning J. Jessen、Damien Barbaras、Matthias Hamburger、Karl Gademann

  DOI：10.1021/ol901277q

  日期：2009.8.6

  An efficient synthesis of all four possible stereoisomers of the neurotrophic amide farinosone C was developed. The absolute and relative configuration was assigned by comparison of synthetic material with a derivatized authentic sample of the natural product. Several derivatives allowed for the generation of preliminary structure activity relationships concerning neurite outgrowth in PC-12 cells, unravelling L-tyrosinol-amide as the pharmacophore.