N¹,N⁵-di-(E)-coumaroyl-spermidine | 114916-04-0

• 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-di-(E)-coumaroyl-spermidine
• 英文别名: (E)-N-[3-[4-aminobutyl-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propyl]-3-(4-hydroxyphenyl)prop-2-enamide
• CAS: 114916-04-0
• 化学式: C₂₅H₃₁N₃O₄
• 分子量: 437.539
• InChiKey: SFMLRCDOOPCKCM-VOMDNODZSA-N

物化性质

• 沸点：
  763.2±60.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N¹,N⁵-di-(E)-coumaroyl-spermidine 在 sodium hydroxide 作用下， 反应 4.33h， 生成 N¹,N⁵,N¹⁰-tribenzoylspermidine
  参考文献：
  名称：

  来自桤木、白桦和紫檀花粉的羟基肉桂酸-亚精酰胺

  摘要：

  摘要 羟基肉桂酸-亚精胺已从花粉中分离出来，并从其 1 H NMR 和质谱数据中鉴定： N 1 , N 5 -di-( E )- p -香豆酰亚精胺来自 Pterocarya fraxinifolia (Lam.) Spach., N 5 , N 10 -di-( E )-feruloylspermidine 来自 Betula verrucosa Ehrh。来自 Alnus glutinosa (L.) Gaertn 的两种 di-(E)-p-香豆酰基亚精胺的混合物。

  DOI：

  10.1016/0031-9422(88)84103-7
• 作为产物：
  描述：

  tert-butyl 4-(3-aminopropylamino)butylcarbamate 在 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 N¹,N⁵-di-(E)-coumaroyl-spermidine
  参考文献：
  名称：

  Synthesis of 13C-dilabeled 4-coumaroylspermidines

  摘要：

  Five C-13-dilabeled constitution isomers of 4-coumaroylspermidines were prepared in nine to eleven steps: N-1,4-di[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (13b), N-1-[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (17b), N-1,8-di[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (20b), N-4-[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (24b) and N-1,4,8-tri[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (26). The two C-13-atoms were subsequently introduced using labeled potassium cyanide. The synthesis proceeds through stepwise construction of the polyamine backbone including protection and deprotection steps of the amino functions. Based on H-1-H-1 NOE interactions, the preliminary study of their binding reveals that 20b binds to tRNA in the. same way as spermidine does, whereas 24b and 26 do not-show any NOE effects with the tRNA protons. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01014-x

文献信息

• The Photoisomerization Behavior of the (4-Hydroxycinnamoyl)-spermidines
  作者：Wenquing Hu、Christa Werner、Manfred Hesse

  DOI：10.1002/hlca.19980810215

  日期：1998.2.4

  explanation for these different behaviors. Furthermore, it was noticed that the (Z) (E) isomerization of the CC bond took place during the purification by reverse-phase high-performance liquid chromatography (RP-HPLC), and the (E)/(Z)-mixture is thus inseparable. The same feature could be observed during the isolation of the (Z,Z)-N,N′-bis[3-(4-hydroxyphenyl)prop-2-enoyl]-spermidines, (Z,Z)-4, (Z,Z)-5, and

  三个单[（E）-3-（4-羟苯基）丙-2-烯酰基]亚精胺1、2和3以及三个双[（E）-3-（4-羟苯基）丙-研究了2-烯酰基]亚精胺4、5和6。在紫外光照射下，合成产物（E）-1几乎可以定量地（> 96％）转化为其异构体（Z）-1。在（E）-2和（E）-3的情况下，（E）/（Z）的混合物约为当应用相同条件时，获得1：2。它们的紫外线光谱的比较为这些不同的行为提供了可能的解释。此外，注意到在通过反相高效液相色谱（RP-HPLC）纯化期间，CC键的（Z）（E）异构化发生，并且（E）/（Z）混合物为因此密不可分。在（Z，Z）-N，N'-双[3-（4-羟基苯基）丙-2-烯酰基]-亚精胺，（Z，Z）-4，（Z，Z）-5和（Z，Z）-6。然而，（Z，Z）-5和（Z，Z）-6的馏分几乎处于纯净状态，并给出了它们的1 -NMR光谱。
• On-Line Coupling of High-Performance Liquid Chromatography to Atmospheric Pressure Chemical Ionization Mass Spectrometry (HPLC/APCI-MS and MS/MS). The Pollen Analysis ofHippeastrum x hortorum (Amaryllidaceae)
  作者：Nikolay Youhnovski、Laurent Bigler、Christa Werner、Manfred Hesse

  DOI：10.1002/(sici)1522-2675(19980909)81:9<1654::aid-hlca1654>3.0.co;2-t

  日期：1998.9.9

  A H2O/MeOH extract of the pollen of Hippeastrum x hortorum (Amaryllidaceae) was analyzed. A mixture of different compounds (at the most 84) was found, namely the geometrically ((E,E), (E,Z), (Z,E), and (Z,Z) and structurally isomeric N,N'-dicoumaroyl (= N,N'-bis[3-(4-hydroxyphenyl)prop-2-enoy]), N,N'-diferuloyl (= N,N'-bis[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]), N,N'-disinapoyl (= N,N'-bis[3-(4-hydroxy-3,5-dimethoxyphenyl) prop-2-enoyl]), N-coumaroyl-N'-feruloyl, and N-feruloyl-N'-sinapoyl derivatives of spermidine (= 4-azaoctane-1,8-diamine = N-(3-aminopropyl)butane-1,4-diamine), Their structures were proven by using on-line-coupled high-performance liquid chromatography and atmospheric-pressure chemical-ionization mass spectrometry (HPLC-UV(DAD)/APCI-MS and MS/MS), UV-induced (E)=(Z) photoisomerization, and catalytic hydrogenation, as well by comparing their spectra and chromatographic behavior with those of synthetic standards. According to the physicochemical properties of these natural compounds, a proposed biological function is discussed.
• Synthesis of 13C-dilabeled 4-coumaroylspermidines
  作者：Hervé Geneste、Manfred Hesse

  DOI：10.1016/s0040-4020(98)01014-x

  日期：1998.12

  Five C-13-dilabeled constitution isomers of 4-coumaroylspermidines were prepared in nine to eleven steps: N-1,4-di[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (13b), N-1-[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (17b), N-1,8-di[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (20b), N-4-[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (24b) and N-1,4,8-tri[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (26). The two C-13-atoms were subsequently introduced using labeled potassium cyanide. The synthesis proceeds through stepwise construction of the polyamine backbone including protection and deprotection steps of the amino functions. Based on H-1-H-1 NOE interactions, the preliminary study of their binding reveals that 20b binds to tRNA in the. same way as spermidine does, whereas 24b and 26 do not-show any NOE effects with the tRNA protons. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Hydroxycinnamic acid-spermidine amides from pollen of Alnus glutinosa, Betula verrucosa and Pterocarya fraxinifolia
  作者：Barbara Meurer、Victor Wray、Rolf Wiermann、Dieter Strack

  DOI：10.1016/0031-9422(88)84103-7

  日期：1988.1

  Abstract Hydroxycinnamic acid—spermidine amides have been isolated from pollen and identified from their 1 H NMR and mass spectral data: N 1 , N 5 -di-( E )- p -coumaroylspermidine from Pterocarya fraxinifolia (Lam.) Spach., N 5 , N 10 -di-( E )-feruloylspermidine from Betula verrucosa Ehrh. a mixture of two di-( E )- p -coumaroylspermidines from Alnus glutinosa (L.) Gaertn.

  摘要 羟基肉桂酸-亚精胺已从花粉中分离出来，并从其 1 H NMR 和质谱数据中鉴定： N 1 , N 5 -di-( E )- p -香豆酰亚精胺来自 Pterocarya fraxinifolia (Lam.) Spach., N 5 , N 10 -di-( E )-feruloylspermidine 来自 Betula verrucosa Ehrh。来自 Alnus glutinosa (L.) Gaertn 的两种 di-(E)-p-香豆酰基亚精胺的混合物。