N¹,N⁵,N¹⁰-(Z)-tri-p-coumaroylspermidine | 131086-78-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N¹,N⁵,N¹⁰-(Z)-tri-p-coumaroylspermidine
• 英文别名: N1,N5,N10-(Z)-tri-p-coumaroylspermidine；(Z)-3-(4-hydroxyphenyl)-N-[4-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-[3-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propyl]amino]butyl]prop-2-enamide
• CAS: 131086-78-7
• 化学式: C₃₄H₃₇N₃O₆
• 分子量: 583.684
• InChiKey: PFDVWJCSCYDRMZ-XWBZMVROSA-N

物化性质

• 熔点：
  176-180 °C
• 沸点：
  954.2±65.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-3-(4-羟基苯基)-N-(4-((E)-3-(4-羟基苯基)丙烯酰氨基)丁基)-N-(3-((E)-3-(4-羟基苯基)丙烯酰氨基)丙基)丙烯酰胺 以 甲醇 为溶剂， 生成 N¹,N⁵-(Z)-N¹⁰-(E)-tri-p-coumaroylspermidine 、 N¹N⁵(Z,Z),N¹⁰(E)-tri-p-coumaroylspermidine 、 、 、 (Z)-3-(4-hydroxyphenyl)-N-[4-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-[3-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propyl]amino]butyl]prop-2-enamide 、 N1(E),N5(Z),N10(E)-tri-p-coumaroylspermidine 、 N¹,N⁵,N¹⁰-(Z)-tri-p-coumaroylspermidine
  参考文献：
  名称：

  The unusual conformational preference of N1,N5,N10-tri-p-coumaroylspermidine E-Z isomers from the Japanese apricot tree, Prunus mume, for the (ZZZ)-form

  摘要：

  The Japanese apricot tree, Prunus mume (Siebold) Siebold & Zucc. cv. Nanko, bears two types of flowers: those with anthers that fluoresce under UV irradiation, and those that do not. The chemical composition of both types of anthers has been investigated: the non-fluorescent anthers contained eight E-Z isomers of N-1,N-5,N-1(0)-tri-p-coumaroylspermidine as major constituents; whereas the fluorescent anthers contained only a limited amount of (ZZZ)-isomer, but relatively large amounts of fluorescent chlorogenic acid, implying the abnormal development of fluorescent anthers. Of these eight E-Z isomers, three were undescribed, and identified as the (ZEZ)-, (ZEE)-, and (EEZ)-forms. Their photoequilibrium ratios were found to be characteristic, wherein the (ZZZ)-isomer predominated over the (EEE). H-1 NMR and NOESY experiments and ab initio molecular orbital calculations indicated that intramolecular T-shaped pi/pi, CH/pi, and OH center dot center dot center dot O = C hydrogen bonding interactions impart an unusual degree of stability to the (ZZZ)-isomer that is sufficient to overcome various factors that favor the (EEE)-form.

  DOI：

  10.1016/j.phytol.2019.02.028