1-二甲氨基-4-甲基萘 | 4523-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-二甲氨基-4-甲基萘
• 英文名称: N,N,4-trimethylnaphthalen-1-amine
• 英文别名: 1-dimethylamino-4-methylnaphthalene
• CAS: 4523-52-8
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: VFRROKGSCDTCBK-UHFFFAOYSA-N

物化性质

• 沸点：
  297.3±9.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 1-二甲氨基-4-甲基萘 在 氧气 、 copper(II) acetate monohydrate 、 溶剂黄146 、 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 24.0h， 以61%的产率得到1,6-dimethylbenzo[cd]indol-2(1H)-one
  参考文献：
  名称：

  C8-H键激活与C2-H键激活：从萘胺到内酰胺

  摘要：

  已经实现了萘胺的Pd催化的选择性胺定向C8-H键官能化/ N-脱烷基羰基化。有人提出将脱烷基反应中的胺基团作为促进这一过程的指导。它...

  DOI：

  10.1039/c6cc06358f
• 作为产物：
  描述：

  1-溴-4-甲基萘 在 iron(III) oxide 、 氨 、 ferric nitrate 作用下， 以 乙醚 为溶剂， 生成 1-二甲氨基-4-甲基萘
  参考文献：
  名称：

  1114.一些萘胺和cen庚胺及其二甲基衍生物的解离常数

  摘要：

  DOI：

  10.1039/jr9650005948

文献信息

• Palladium-Catalyzed Highly Regioselective Aromatic Substitution of Benzylic Ammonium Salts with Amines
  作者：Ya-Nan Xu、Meng-Zeng Zhu、Yu-Kun Lin、Shi-Kai Tian

  DOI：10.1021/acs.orglett.9b02820

  日期：2019.9.6

  An unprecedented aromatic substitution reaction of benzylic ammonium salts has been developed through palladium-catalyzed C-N bond cleavage. A range of primary and secondary amines participated in a palladium-catalyzed aromatic substitution reaction of benzylic ammonium salts, delivering sterically hindered aromatic amines in moderate to excellent yields with extremely high regioselectivity. Preliminary

  通过钯催化的CN键裂解，已经开发出前所未有的苄基铵盐的芳族取代反应。一系列伯胺和仲胺参与了钯催化的苄基铵盐的芳族取代反应，以中等至极好的收率提供了位阻芳族胺，且具有极高的区域选择性。初步的机理研究成功地鉴定出π-苄基钯配合物和γ-乙烯基烯丙基胺为关键中间体。该研究为在芳族取代反应中使用苄基铵盐铺平了道路。
• Internal conversion in 4-substituted 1-naphthylamines. Influence of the electron donor/acceptor substituent character
  作者：Kengo Suzuki、Attila Demeter、Wolfgang Kühnle、Erich Tauer、Klaas A. Zachariasse、Seiji Tobita、Haruo Shizuka

  DOI：10.1039/a908924a

  日期：——

  The thermally activated internal conversion (IC) taking place in 4-substituted 1-(dimethylamino)naphthalenes (14DMX) and 1-aminonaphthalenes (14ANX) with X=CN, Cl, H, CH3 and OCH3 was investigated in three solvents spanning the polarity scale, hexane, diethyl ether and acetonitrile. In both series 14DMX and 14ANX, the efficiency of the IC reaction decreases substantially when X changes from CN to OCH3, the order in which the electron donor character of the 4-substituent increases. Considerably larger IC reaction rate constants are obtained for the first group of compounds. This difference is connected with the ground state structure of the amino group, which is more strongly twisted for 14DMX (ca. 60°) than for 14ANX (ca. 20°), whereas both sets of 1-naphthylamines are planarised in the S1 excited state. The IC process slows down with increasing solvent polarity for each of the 14DMX and 14ANX molecules. The substituent X and the solvent polarity mainly affect the IC activation energy EIC. With 14DMX in hexane, EIC increases from 10 kJ mol−1 for X=CN to 34 kJ mol−1 for X=OCH3, whereas with, e.g., 14DMCL a solvent polarity dependent increase of EIC from 16 kJ mol−1 in hexane to 28 kJ mol−1 in acetonitrile is observed. The height of the barrier EIC is governed by the energy gap ΔE(S1,S2) between the two lowest excited singlet states. The influence of ΔE(S1,S2) on EIC is attributed to vibronic coupling caused by the proximity of the S1 and S2 states, which flattens the S1 potential energy surface and thereby lowers the IC barrier when ΔE(S1,S2) becomes smaller. It is assumed that the IC reaction of the 1-naphthylamines passes through a conical intersection, which exists as a consequence of the relative displacement of the S1 and S0 surfaces caused by the different amino twist angles in the two states.

  对4-取代的1-(二甲氨基)萘(14DMX)和1-氨基萘(14ANX，X=CN、Cl、H、CH3和OCH3)中发生的热激活内部转换（IC）进行了研究，实验在三种不同极性的溶剂中进行，分别是己烷、二乙醚和乙腈。在14DMX和14ANX两系列化合物中，当X从CN变化为OCH3时，IC反应的效率显著降低，这一变化的顺序与4-取代基的电子给予特性逐渐增强有关。对于第一组化合物，获得的IC反应速率常数明显更大。这个差异与氨基的基态结构有关，其中14DMX的扭曲程度（约60°）显著高于14ANX（约20°），而在激发态S1中，这两类1-萘基胺的平面性则得以保持。对于每个14DMX和14ANX分子来说，IC过程随着溶剂极性的增加而减慢。取代基X和溶剂极性主要影响IC的激活能EIC。在己烷中的14DMX，EIC从X=CN的10 kJ mol−1增加到X=OCH3的34 kJ mol−1，而以14DMCL为例，EIC在己烷中观察到从16 kJ mol−1到在乙腈中达到28 kJ mol−1的随着溶剂极性增加而变化。EIC的能垒高度由两个最低激发单态之间的能量间隙ΔE(S1,S2)所主导。ΔE(S1,S2)对EIC的影响归因于由于S1和S2状态的近似而导致的振动耦合，这使得S1的势能曲面变平，从而当ΔE(S1,S2)减小时，降低了IC的能垒。假设1-萘基胺的IC反应是通过锥形交叉点进行的，这一交叉点是由于两种状态中不同的氨基扭转角引起的S1和S0表面的相对位移而存在的。
• [EN] COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PAIN<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DE LA DOULEUR
  申请人：UNIV STRASBOURG

  公开号：WO2019149965A1

  公开（公告）日：2019-08-08

  The invention relates to compounds, pyridine derivatives, and pharmaceutical 10 compositions containing same for use in the treatment of pain. It also relates to specific compounds, compositions comprising the same and uses thereof, in particular in the treatment of pain.

  这项发明涉及化合物、吡啶衍生物和含有这些化合物的药物组合物，用于治疗疼痛。它还涉及特定化合物、包含这些化合物的组合物及其用途，特别是在疼痛治疗中的应用。
• DYE FOR PHOTOELECTRIC CONVERSION, SEMICONDUCTOR ELECTRODE, PHOTOELECTRIC CONVERSION ELEMENT, SOLAR CELL, AND NOVEL PYRROLINE-BASED COMPOUND
  申请人：Maeda Katsumi

  公开号：US20130118570A1

  公开（公告）日：2013-05-16

  Provided is a dye for photoelectric conversion containing at least one or more kind of a compound represented by the following General Formula (1) (in Formula (1), R 1 and R 2 represent any one of —CN, —SO 2 R, —COOR, and —CONR 2 (R represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, or an aryl group); R 3 represents a direct bond or a substituted or unsubstituted alkylene group; X represents an acidic group; and D represents an organic group having an electron donating substituent or a substituted or unsubstituted heterocyclic group).

  提供一种用于光电转换的染料，其含有至少一种或多种由以下通式（1）表示的化合物（在式（1）中，R1和R2代表-CN、-SO2R、-COOR和-CONR2中的任意一种（其中R代表氢原子、取代或未取代的烷基、环烷基或芳基）；R3代表直接键或取代或未取代的烷基烯基；X代表酸性基团；D代表具有电子给体取代基或取代或未取代的杂环基团的有机基团）。
• Reverse-turn mimetics and method relating thereto
  申请人：Moon Hwan Sung

  公开号：US20060084655A1

  公开（公告）日：2006-04-20

  Conformationally constrained compounds that mimic the secondary structure of reverse-turn regions of biologically active peptides and proteins are disclosed. Such reverse-turn mimetic structures have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the reverse-turn mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members. The invention also relates to the use of such compounds for inhibiting or treating disorders modulated by Wnt-signaling pathway, such as cancer, especially colorectal cancer, restenosis associated with angioplasty, polycystic kidney disease, aberrant angiogenesis disease, rheumatoid arthritis disease, tuberous sclerosis complex, Alzheimer's disease, excess hair growth or loss, or ulcerative colitis.

  本发明揭示了限制构象的化合物，其模拟具有生物活性的肽和蛋白质的反转区域的二级结构。这种反转模拟结构在广泛的领域中具有实用性，包括用作诊断和治疗剂。本发明还揭示了包含此类反转模拟结构的库，以及筛选这些库以识别具有生物活性成员的方法。本发明还涉及使用这种化合物来抑制或治疗Wnt信号通路调节的疾病，如癌症，特别是结直肠癌，与血管成形术相关的再狭窄，多囊肾病，异常血管生成疾病，类风湿性关节炎疾病，结节性硬化症，阿尔茨海默病，过多或过少的毛发生长或溃疡性结肠炎。