3-(9-anthryl)propylamine | 150147-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-(9-anthryl)propylamine
• 英文别名: 3-Anthracen-9-yl-propylamine；3-anthracen-9-ylpropan-1-amine
• CAS: 150147-40-3
• 化学式: C₁₇H₁₇N
• 分子量: 235.329
• InChiKey: GVHAGOANZFMSCM-UHFFFAOYSA-N

物化性质

• 熔点：
  >236 °C (decomp)(Solv: methanol (67-56-1); ethyl acetate (141-78-6))
• 沸点：
  425.8±24.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(9-anthryl)propylamine 在 二氧化碳 作用下， 以 二甲基亚砜 为溶剂， 反应 2.3h， 以93%的产率得到5,12:6,11-di-o-benzenodibenzo[a,e]cyclooctene-5,11(6H,12H)-bis(propanamine)
  参考文献：
  名称：

  Solvent-dependent effect by carbon dioxide on the photoreactions of (9-anthryl)alkylamines

  摘要：

  The effect Of CO2 on a photoreaction was first studied systematically by using (9-anthryl)alkylamines (APA, AEA, and AMA) as the starting compound. From close scrutiny of the results, the CO, effect was clearly observed and was well rationalized by the previously reported novel solvent dependence of the amine-CO2 reversible reactions. For instance, the yield of the dimer (h-t from APA or AEA, h-t+h-h from AMA) obtained in MeOH or DMSO was higher under CO2 than under argon and this was ascribed to formation of either ammonium bicarbonate/carbonate in MeOH or carbamic acid in DMSO, which will prevent the nitrogen lone pair from being involved in electron-transfer reactions. In fact, the electron-transfer side reactions producing 1-3 in DMSO were strongly inhibited under CO2. Also, due to formation of noncovalent linkage between the ammonium cation and the carbamate anion in 2-PrOH, the proportion of h-h relative to h-t produced from AMA in 2-PrOH was increased by carrying out the reaction under CO2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.069
• 作为产物：
  描述：

  (z)-3-(Anthracen-9-yl)acrylonitrile 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 生成 3-(9-anthryl)propylamine
  参考文献：
  名称：

  DNA小槽中蒽基探针对腺嘌呤-胸腺嘧啶碱基对的识别

  摘要：

  此处报道了几何异构体9（3-氨基丙基）蒽（APAC）和9（N-乙基）氨基甲基蒽（N-Et-AMAC）的合成和DNA结合特性。APAC的氨丙基侧链可以将氨基官能团定位在DNA凹槽中，以便与杂环碱基进行氢键键合。相反，N-Et-AMAC的N-乙基-氨基甲基侧链太短而无法在凹槽中接触。使用吸收，荧光，圆二色性（CD），单重态-单重态能量转移和DNA熔解实验检查DNA的结合特性。除了小牛胸腺DNA（CTDNA），我们还检查了poly（dA-dT），poly（dG-dC），poly（dA）-poly（dT）和poly（dI-dC）。光谱和热学研究表明蒽基探针插入到螺旋中。然而，结合特性取决于侧链以及DNA序列。APAC与poly（dA-dT）的结合比poly（dG-dC）的结合要好3.4倍，而N-Et-AMAC（APAC的几何异构体）的结合要好，与所检查的所有DNA聚合物几乎相同。通过使用肌苷-胞嘧

  DOI：

  10.1016/s0040-4020(00)00526-3

文献信息

• N-Substituent Effects in the Selective Delivery of Polyamine Conjugates into Cells Containing Active Polyamine Transporters
  作者：Richard Andrew Gardner、Jean-Guy Delcros、Fanta Konate、Fred Breitbeil、Bénédicte Martin、Michael Sigman、Min Huang、Phanstiel

  DOI：10.1021/jm0497040

  日期：2004.11.1

  N(1)-anthracen-9-ylmethyl, N(1)-2-(anthracen-9-yl)ethyl, N(1)-3-(anthracen-9-yl)propyl, and pyren-1-ylmethyl. The polyamine architecture was also altered and ranged from diamine to triamine and tetraamine systems. Biological activities in L1210 (murine leukemia), Chinese hamster ovary (CHO), and CHO's polyamine transport-deficient mutant (CHO-MG) cell lines were investigated via IC(50) cytotoxicity determinations

  合成了几种含有各种芳环系统的N（1）-芳基烷基多胺作为它们各自的HCl盐。评估的N（1）取代基大小从N（1）-苄基，N（1）-萘-1-基甲基，N（1）-2-（萘-1-基）乙基，N（1） -3-（萘-1-基）丙基，N（1）-蒽-9-基甲基，N（1）-2-（蒽-9-基）乙基，N（1）-3-（蒽-9 -基）丙基和pyr-1-基甲基。多胺的结构也被改变，范围从二胺到三胺和四胺体系。通过IC（50）细胞毒性测定研究了L1210（鼠白血病），中国仓鼠卵巢（CHO）和CHO的多胺转运缺陷型突变体（CHO-MG）细胞系的生物学活性。L1210细胞中亚精胺摄取的K（i）值也已确定。N（1）-芳基烷基取代基的大小以及所用的多胺序列直接影响到观察到的细胞毒性谱。如CHO / CHO-MG细胞毒性筛选所示，比乙烯长的N（1）-系链显示出对多胺转运蛋白（PAT）的选择性显着丧失。总之，对于N（1）取代基的大小有明确
• Synthesis and Biological Studies of Pyrazolyl-Diamine Pt^IIComplexes Containing Polyaromatic DNA-Binding Groups
  作者：Sofia Gama、Filipa Mendes、Teresa Esteves、Fernanda Marques、António Matos、José Rino、Joana Coimbra、Mauro Ravera、Elisabetta Gabano、Isabel Santos、António Paulo

  DOI：10.1002/cbic.201200472

  日期：2012.11.5

  Platinum and intercalation: To achieve synergistic effects between intercalation and DNA platination, new pyrazolyl‐diamine PtII complexes containing anthracenyl (L2Pt) or acridine orange (L3Pt) groups were created, and their DNA interaction and cytotoxicity were investigated. L2Pt showed the highest cytotoxic potency, probably due to a different mode of action from those of L3Pt or cis‐DDP.

  铂和插层：为了实现插层和DNA电镀之间的协同作用，创建了新的含蒽基（L 2 Pt）或a啶橙（L 3 Pt）基的吡唑基-二胺Pt II复合物，并研究了它们的DNA相互作用和细胞毒性。L 2 Pt表现出最高的细胞毒性，这可能是由于其与L 3 Pt或顺式-DDP的作用方式不同。
• Synthesis and Characterization of Solution-Processable Core-Cyanated Perylene-3,4;9,10-bis(dicarboximide) Derivatives
  作者：Shinji Ando、Antonio Facchetti、Tobin J. Marks

  DOI：10.1021/ol1020338

  日期：2010.11.5

  Core-cyanated perylene-3,4;9,10-bis(carboxyimide) derivatives N-functionalized with tethered anthracenes (PDI3A-CN2, PDI4A-CN2) and the corresponding solution-processable cycloadduct precursors (PDI3A-CA-CN2, PDI4A-CA-CN2) were synthesized and their optical, electrochemical, and thermal properties characterized. These derivatives exhibit HOMO−LUMO energy gaps of ∼2.1−2.3 eV and first reduction potentials

  用链状蒽（PDI3A-CN 2，PDI4A-CN 2）和相应的溶液可加工的环加合物前体（PDI3A-CA-CN 2）N-官能化的核心氰化per 3,4; 9,10-双（羧酰亚胺）衍生物，PDI4A-CA-CN 2）的合成和它们的光学，电化学，和热性能表征。这些导数相对于SCE表现出〜2.1-2.3 eV的HOMO-LUMO能隙和-50至-150 mV的第一还原电位。所述PDI3A-CN 2和PDI4A-CN 2个cycloadducts可溶于普通的有机溶剂（> 50毫克/毫升），以及相应的旋涂膜转换为热退火后的PDI3A-CN 2和PDI4A-CN 2膜。
• Organic semiconductor materials and precursors thereof
  申请人：Facchetti Antonio

  公开号：US20080249309A1

  公开（公告）日：2008-10-09

  The present teachings provide novel organic semiconductor compounds and their soluble precursors, methods for preparing these compounds and precursors, as well as compositions, materials, articles, structures, and devices that incorporate such compounds.

  本教学提供了新型有机半导体化合物及其可溶性前体，制备这些化合物和前体的方法，以及包含这些化合物的组合物、材料、文章、结构和设备。
• WO2008/91670
  申请人：——

  公开号：——

  公开（公告）日：——