N-(indole-3-ethyl)-Δ2,11-enaminousnic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(indole-3-ethyl)-Δ2,11-enaminousnic acid
• 英文别名: (9bR)-6-acetyl-7,9-dihydroxy-2-[1-[2-(1H-indol-3-yl)ethylamino]ethylidene]-8,9b-dimethyldibenzofuran-1,3-dione
• 化学式: C₂₈H₂₆N₂O₆
• 分子量: 486.524
• InChiKey: KGLBHXZKLBDNOP-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  128.72
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  sodium tetrachloropalladate(II) 、 N-(indole-3-ethyl)-Δ2,11-enaminousnic acid 、 水 在 (CH₃)3COK 作用下， 以 二甲基亚砜 为溶剂， 以19%的产率得到[Pd2(N-(indole-3-ethyl)-Δ2,11-enaminousnic acid(-2H))2]*0.5H2O
  参考文献：
  名称：

  Indole Rings in Palladium(II) Complexes. Dual Mode of Metal Binding and Aromatic Ring Stacking Causing syn−anti Isomerism

  摘要：

  In view of the interesting metal-binding properties of lichen substances and the indole ring as a potential ligand, we studied the Pd(II) complexes of indole-containing ligands, N-(indole-3-ethyl)-Delta(2,11)-enaminousnic acid (IEU) and 4-[2-(indol-3-yl)-ethylamino]pent-3-en-2-one (IEP) obtained by condensation of tryptamine with usnic acid and its model acetylacetone, respectively. Reactions of Pd( II) with IEU and IEP gave isomeric complexes resulting from coordination of the C( 3) atom of the indole ring in the 3H-indole form, Pd-2(IEUH-2)(2) (1 and 2) and Pd-2(IEPH-2)(2) (3 and 4) (IEUH-2 and IEPH-2 denote doubly deprotonated forms of IEU and IEP, respectively). Complexes 1-4 were determined, from the NMR and MS spectra, to have dimeric structures doubly bridged by the indole rings, which were stacked in different orientations. X-ray crystal structure analysis of 3 and 4 established that they are indole-bridged dimers of the [C, N, O]-donor palladacycles with the Pd(II) centers in a square-planar geometry formed by a CN2O donor set and are anti and synisomers with respect to the bridging indole rings, respectively. On the basis of the spectral similarity with 4, 1 and 2 were concluded to be stereoisomers assuming the synform with the same donor set. The results demonstrate the metal binding and stacking abilities of the indole ring and the stereoisomerism from the sp(3) C(3) atom formed upon coordination.

  DOI：

  10.1021/ic060595k
• 作为产物：
  描述：

  色胺 、 (+)-usnic acid 以 乙醇 为溶剂， 反应 21.0h， 以93%的产率得到N-(indole-3-ethyl)-Δ2,11-enaminousnic acid
  参考文献：
  名称：

  [EN] DIBENZOFURAN DERIVATIVES WITH ANTIBACTERIAL AND WOUND-HEALING ACTIVITY
  [FR] DÉRIVÉS DE DIBENZOFURANNE À ACTIVITÉ ANTIBACTÉRIENNE ET DE CICATRISATION DE PLAIES

  摘要：

  揭示了乌司酸的二苯并呋喃衍生物，以及它们的组合物，并将其用于具有抗菌、再生和抗衰老作用的皮肤科或化妆品配方中。

  公开号：

  WO2013189950A1