methyl 13-amino-deisopropyldehydroabietate | 100101-53-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 13-amino-deisopropyldehydroabietate
• 英文别名: methyl 13-aminodeisopropyldehydroabietate；13-amino-podocarpa-8,11,13-trien-15-oic acid methyl ester；13-Amino-podocarpa-8,11,13-trien-15-saeure-methylester；methyl (1R,4aS,10aR)-7-amino-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
• CAS: 100101-53-9
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: WZCAIMSEVNXWIM-KBAYOESNSA-N

物化性质

• 沸点：
  405.8±45.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 13-amino-deisopropyldehydroabietate 在 三叔丁基膦 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 邻二甲苯 为溶剂， 生成 methyl (1R,4aS,10aR)-1,4a-dimethyl-7-(N-naphthalen-1-ylanilino)-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylate
  参考文献：
  名称：

  Synthesis and properties of new luminescent hole transporting materials of triarylamine with dehydroabietic acid methyl ester moieties

  摘要：

  A series of triarylamines based on dehydroabietic acid methyl ester moieties (6a-h) were synthesized for possible application as hole transporting materials for organic electroluminescent devices. The target compounds were characterized by elemental analysis, FT-IR, NMR, and mass spectrometry. Their optical, electrochemical, and thermal properties were investigated using UV-vis, PL spectroscopy, cyclic voltammetry (CV), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC), respectively. CV measurements show that the compounds present suitable HOMO values (in a range of -4.63 to -5.11 eV) for hole injection, which is confirmed by theoretical calculations. All compounds were thermally stable. Organic light-emitting diode devices having 6f, 6g, and 6h as a hole transporting layer showed better performance of maximum brightness, turn-on voltage, and maximum luminous efficiency than a comparable device NPB. These compounds could be excellent candidates for applications in OLED devices. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.071
• 作为产物：
  描述：

  (4aS)-1,4a-dimethyl-(4ar,10at)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1t,7-dicarboxylic acid-1-methyl ester 在 氯化亚砜 、 sodium azide 作用下， 生成 methyl 13-amino-deisopropyldehydroabietate
  参考文献：
  名称：

  Ohta, Pharmaceutical Bulletin, 1956, vol. 4, p. 273,275

  摘要：

  DOI：

文献信息

• Synthesis, spectroscopy, photophysics and thermal behaviour of stilbene-based triarylamines with dehydroabietic acid methyl ester moieties
  作者：Bárbara Gigante、M. Alexandra Esteves、N. Pires、Matthew L. Davies、Peter Douglas、Sofia M. Fonseca、Hugh D. Burrows、Ricardo A. E. Castro、João Pina、João Seixas de Melo

  DOI：10.1039/b815711a

  日期：——

  Novel stilbene-based triarylamines with dehydroabietic acid methyl ester moieties have been synthesised by palladium catalysed C–N coupling reactions. The presence of the bulky dehydroabietic acid group increases solubility, hinders crystallisation and permits their sublimation while preserving their electronic and optical characteristics. This makes them good candidates for various molecular electronic applications. We report a detailed characterisation of their electrochemical, spectroscopic and photophysical properties. In addition, the thermal stability and behaviour is discussed with reference to the potential for preparation of stable thin films.

  已合成以脱氢松香酸甲酯为取代基的新型苯乙烯基三芳胺，采用钯催化的C–N偶联反应。庞大的脱氢松香酸基团的存在增加了溶解度，抑制了结晶，并使其在保持电子和光学特性的同时能够升华。这使得它们成为各种分子电子应用的良好候选者。我们报告了对其电化学、光谱和光物理特性的详细表征。此外，还讨论了热稳定性和行为，以及制备稳定薄膜的潜力。
• Photoresponsive Foams Generated by a Rigid Surfactant Derived from Dehydroabietic Acid
  作者：Lan Lei、Danhua Xie、Binglei Song、Jianzhong Jiang、Xiaomei Pei、Zhenggang Cui

  DOI：10.1021/acs.langmuir.7b00934

  日期：2017.8.15

  Innovation in the structure of surfactants is crucial to the construction of a surfactant-based system with intriguing properties. With dehydroabietic acid as a starting material, a nearly totally rigid azobenzene surfactant (R-azo-Na) was synthesized. The trans-R-azo-Na formed stable foams with half-lives of 636, 656, 976, and 872 min for 0.3, 1, 2, and 4 mmol·L–1 aqueous solutions, respectively.

  表面活性剂结构的创新对于构建具有吸引力的基于表面活性剂的体系至关重要。以脱氢松香酸为起始原料，合成了几乎完全刚性的偶氮苯表面活性剂（R-azo-Na）。所述反式-R-偶氮娜形成稳定的泡沫与636，656，976的半衰期，和872分钟为0.3，1，2，和4mmol·L -1分别水溶液，。在紫外光照射下，观察到泡沫快速塌陷，显示出原位响应。反式-R-偶氮-Na优异的泡沫稳定性导致极高的光响应效率。如动态表面张力和脉冲场梯度NMR方法所揭示的那样，在吸附/解吸过程中存在明显的能垒。空气/水界面上的反式-R-偶氮-钠 因此，由反式-R-偶氮-Na形成的泡沫对于粗化过程是稳定的。结果揭示了具有刚性疏水骨架的表面活性剂的独特光响应性能，并为引起表面活性剂聚集的结构提供了新的见解。