2,4-二甲基-6-苯基吡啶 | 27068-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,4-二甲基-6-苯基吡啶
• 英文名称: 4,6-dimethyl-2-phenyl pyridine
• 英文别名: 2,4-dimethyl-6-phenylpyridine；2-phenyl-4,6-dimethylpyridine；4,6-dimethyl-2-phenylpyridine；2,4-dimethyl-6-phenyl-pyridine；2,4-Dimethyl-6-phenyl-pyridin；2,4-Dimethyl-6-phenylpyridin
• CAS: 27068-65-1
• 化学式: C₁₃H₁₃N
• mdl: MFCD11044332
• 分子量: 183.253
• InChiKey: YRGAWNRLOJMKTR-UHFFFAOYSA-N

物化性质

• 沸点：
  130-134 °C(Press: 4 Torr)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2,4-二甲基-6-苯基吡啶 在 potassium permanganate 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 生成 (6-phenylpyridine-2,4-diyl)dimethanol
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Phenylenebis(methylene)- Linked Bis-tetraazamacrocycles That Inhibit Human Immunodeficiency Virus Replication. 2. Effect of Heteroaromatic Linkers on the Activity of Bicyclams

  摘要：

  A series of bicyclam analogs connected through a heteroaromatic linker have been synthesized and evaluated for their inhibitory effects on HIV-1 (IIIB) and HIV-2 (ROD) replication in MT-4 cells. The activity of pyridine- and pyrazine-linked bicyclams was found to be highly dependent upon the substitution of the heteroaromatic linker connecting the cyclam rings. For example, 2,6- and 3,5-pyridine-linked bicyclams were potent inhibitors of HIV-1 and HIV-2 replication, whereas the 2,5- and 2,4-substituted pyridine-linked compounds exhibited substantially reduced activity and, in addition, were found to be highly toxic to MT-4 cells. We have subsequently discovered that these effects are not unique; amino-substituted linkers also have the potential to deactivate phenylenebis(methylene)-linked bicyclams. A model is proposed to explain the deactivating effects of the pyridine group in certain substitution patterns based on the ability of the pyridine nitrogen to participate in pendant conformations (complexation) with the adjacent azamacrocyclic ring, which may involve hydrogen bonding or coordination to a transition metal. The introduction of a sterically hindering group such as phenyl at the 6-position of the 2,4-substituted pyridine-linked bicyclam appears to prevent pendant conformations, providing an analog with comparable anti-HIV-1 and anti-HIV-2 activities to the parent m-phenylenebis(methylene)-linked bicyclam, The results of this study have been used to develop a quantitative structure-activity relationship model with improved predictive capability in order to aid the design of antiviral bis-azamacrocyclic analogs.

  DOI：

  10.1021/jm950584t
• 作为产物：
  描述：

  1-(2-methyl-1,3-dioxolan-2-yl)propan-2-one 在 palladium on activated charcoal 、 盐酸羟胺 、 氢气 、 sodium acetate 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 magnesium 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 20.5h， 生成 2,4-二甲基-6-苯基吡啶
  参考文献：
  名称：

  由1,5-二酮烷烃改进的2,4,6-三烷基吡啶的合成：阿尼巴明的总合成

  摘要：

  迄今为止，已经开发了许多吡啶合成物。在这项研究中，我们集中于吡啶与1,5-二酮衍生物和羟胺的合成。在碱性或酸性条件下处理简单的1，5-二酮烷烃和羟胺可得到没有任何吡啶化合物的羟醛加合物。但是，通过筛选反应条件，我们发现酸性条件是通过衍生自1，5-二酮烷的肟中间体的形成允许形成相应的吡啶衍生物。这是由非常简单的1，5-二酮烷烃合成2,4,6-三烷基吡啶的第一个例子。为了证明该反应的实用性，我们证明了吡啶衍生物的合成和6-取代的吡啶基-天然产物阿尼巴明的总合成。通过遵循上述方法，使用报道的化合物作为起始原料，以12％的收率得到产物，实现了该目的。

  DOI：

  10.1039/c8ob02723d

文献信息

• [EN] BISIMIDAZOLODIAZOCINES<br/>[FR] BIS-IMIDAZOLO-DIAZOCINES
  申请人：IDEMITSU KOSAN CO

  公开号：WO2016125110A1

  公开（公告）日：2016-08-11

  The present invention relates to an organic electronic device, preferably an OLED, comprising a Bisimidazolodiazocine of formula (I) charge transport layer, a charge/exciton blocker layer, or an emitting layer comprising the Bisimidazolodiazocine; an apparatus selected from the group consisting of stationary visual display units; mobile visual display units; illumination units; keyboards; items of clothing; furniture; wallpaper, comprising the inventive organic electronic device, or the inventive charge transport layer, the charge/exciton blocker layer, or the emitting layer; the use of the Bisimidazolodiazocines for electrophotographic photoreceptors, photoelectric converters, organic solar cells, switching elements, organic light emitting field effect transistors, image sensors, dye lasers and electroluminescent devices; a process for the production of the Bisimidazolodiazocines and specific Bisimidazolodiazocines..

  本发明涉及一种有机电子器件，优选为OLED，包括式(I)的双咪唑二唑啉的电荷传输层，电荷/激子阻挡层，或包括双咪唑二唑啉的发射层；选自固定视觉显示单元组、移动视觉显示单元、照明单元、键盘、服装、家具、墙纸的装置，包括所述创新的有机电子器件，或创新的电荷传输层、电荷/激子阻挡层或发射层；双咪唑二唑啉用于电子照相感光鼓、光电转换器、有机太阳能电池、开关元件、有机发光场效应晶体管、图像传感器、染料激光器和电致发光器件的用途；一种生产双咪唑二唑啉和特定双咪唑二唑啉的方法。
• Alcohols as alkylating agents in heteroarene C–H functionalization
  作者：Jian Jin、David W. C. MacMillan

  DOI：10.1038/nature14885

  日期：2015.9

  The biochemical process of spin-centre shift is used to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors; this represents the first broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. A central reaction in DNA biosynthesis is ribonucleotide deoxygenation via the radical-mediated elimination of H2O, which is an example of 'spin-centre shift' (SCS), during which an alcohol C–O bond is cleaved to produce in a carbon-centred radical intermediate. Although SCS is a well-understood biochemical process, it is underutilized by the synthetic organic chemistry community. Here Jian Jin and David MacMillan show that it is possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylations using alcohols as radical precursors. This method represents the first broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the merger of photoredox and hydrogen atom transfer catalysis. Redox processes and radical intermediates are found in many biochemical processes, including deoxyribonucleotide synthesis and oxidative DNA damage1. One of the core principles underlying DNA biosynthesis is the radical-mediated elimination of H2O to deoxygenate ribonucleotides, an example of ‘spin-centre shift’2, during which an alcohol C–O bond is cleaved, resulting in a carbon-centred radical intermediate. Although spin-centre shift is a well-understood biochemical process, it is underused by the synthetic organic chemistry community. We wondered whether it would be possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors. Because conventional radical-based alkylation methods require the use of stoichiometric oxidants, increased temperatures or peroxides3,4,5,6,7, a mild protocol using simple and abundant alkylating agents would have considerable use in the synthesis of diversely functionalized pharmacophores. Here we describe the development of a dual catalytic alkylation of heteroarenes, using alcohols as mild alkylating reagents. This method represents the first, to our knowledge, broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. The value of this multi-catalytic protocol has been demonstrated through the late-stage functionalization of the medicinal agents, fasudil and milrinone.

  利用自旋中心转移的生化过程，通过醇作为自由基前体，可以实现温和的、非传统的烷基化反应。这在合成有机化学领域尚未得到充分应用。本文中Jin Jian和David MacMillan展示了一种方法，即利用这一自然发生的自旋中心转移过程，以醇作为自由基前体，实现温和、非传统的烷基化反应。这种方法首次实现了在广泛应用上将非活化醇作为潜在烷基化试剂，其核心是通过光氧化还原与氢原子转移催化的结合来实现。氧化还原过程和自由基中间体在很多生化过程中都存在，包括脱氧核糖核酸的合成和氧化性DNA损伤。DNA生物合成的关键原理之一就是通过自由基介导的水分子消除反应来脱氧核糖核苷酸，这也是"自旋中心转移"的一个例子。在这个过程中，醇的C-O键断裂，形成碳中心的自由基中间产物。虽然自旋中心转移是一个广为人知的生化过程，但在合成有机化学领域，这一方法尚未得到广泛应用。我们想知道是否有可能利用这个自然发生的自旋中心转移过程，以醇作为自由基前体，实现温和、非传统的烷基化反应。传统的基于自由基的烷基化方法通常需要使用化学计量的氧化剂、提高温度或使用过氧化物，因此一个使用简单且丰富的烷基化试剂的温和协议在合成多样功能化的药物分子上具有很大的应用价值。在这里，我们描述了一种使用醇作为温和烷基化试剂的双催化烷基化杂芳烃的方法。据我们所知，这代表了首次在广泛应用上将非活化醇作为潜在烷基化试剂，其成功在于实现了光氧化还原与氢原子转移催化的结合。该多催化协议的价值已通过药物分子法舒地尔和米力农的后期功能化得到展示。
• The ring transformation of 1,2,3-triazines.
  作者：Takashi ITOH、Mamiko OKADA、Kazuhiro NAGATA、Kentaro YAMAGUCHI、Akio OHSAWA

  DOI：10.1248/cpb.38.2108

  日期：——

  Monocyclic 1, 2, 3-triazines reacted with electron rich dienophiles to give pyridines and pyridazines. 4, 6-Disubstituted 1, 2, 3-triazine was denitrogenated to the azete intermediate, which afforded isomeric pyridines. 2, 5-Dihydrotriazines were oxidized by m-chloroperbenzoic acid to give 1, 2, 3-triazoles. Ring transformations of other triazine derivatives are also reported.

  富电子的双烯亲电试剂与单环1, 2, 3-三嗪反应生成吡啶和吡啶嗪。4, 6-二取代的1, 2, 3-三嗪经过脱氮作用生成偶氮中间体，进而得到异构吡啶。2, 5-二氢三嗪被间氯过氧苯甲酸氧化生成1, 2, 3-三氮唑。还报道了其他三嗪衍生物的环转换反应。
• Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH
  作者：Wenbo Liu、Xiaobo Yang、Zhong-Zhen Zhou、Chao-Jun Li

  DOI：10.1016/j.chempr.2017.03.009

  日期：2017.5

  Heteroarene methylation utilizing a cheap and safe methylation source without involving transition metals represents an important yet challenging objective. Here, a simple and clean catalyst-free protocol for the methylation of various heteroarenes (including six- and five-membered types) is described under light irradiation. This protocol employs cheap, readily available, and abundant MeOH as both

  利用便宜且安全的甲基化来源而不涉及过渡金属的杂芳烃甲基化代表了重要但具有挑战性的目标。在此，描述了在光照射下用于各种杂芳烃（包括六元和五元类型）甲基化的简单，清洁的无催化剂方案。该方案采用廉价，易于获得的丰富甲醇作为溶剂和甲基化来源。发现添加二氯甲烷（DCM）作为助溶剂可以显着提高甲基化产物的产率。带有各种官能团的杂芳烃可以成功地被甲基化和三氘代甲基化。
• PYRIDINYL MODULATORS OF gamma-SECRETASE
  申请人：Lu Tianbao

  公开号：US20100022583A1

  公开（公告）日：2010-01-28

  The present invention relates to compounds of Formula I as shown below, wherein the definitions of A, X, R 1 R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are provided in the specification. Compounds of Formula I are useful for the treatment of diseases associated with γ-secretase activity, including Alzheimer's disease.

  本发明涉及如下所示的Formula I化合物，其中A、X、R1、R2、R3、R4、R5、R6、R7、R8和R9的定义在说明书中提供。Formula I化合物对于治疗与γ-分泌酶活性相关的疾病，包括阿尔茨海默病，具有用处。