2,3,4-trimethoxyphenanthrene | 74825-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,3,4-trimethoxyphenanthrene
• CAS: 74825-06-2
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: NQFCAXUJIOVNPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 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：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethoxyphenanthrene 在 四氧化锇 、 lithium aluminium tetrahydride 、 三氧化硫吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 100.25h， 生成
  参考文献：
  名称：

  Synthesis of 2,2'-diacyl-1,1'-biaryls. Regiocontrolled protection of ketones in unsymmetrically substituted 9,10-phenanthrenequinones

  摘要：

  DOI：

  10.1021/jo01311a034
• 作为产物：
  描述：

  1,2,3-三甲氧基-5-苯乙烯基苯 在 Cu(DPEPhos)(neo)BF₄ 、 碘 、 methyloxirane 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以23%的产率得到2,3,4-trimethoxyphenanthrene
  参考文献：
  名称：

  朝着可见光介导的光环化：用于[5] Helicene的合成的基于铜的敏化剂

  摘要：

  已经开发出使用铜基敏化剂7的[5]螺旋烯的光化学合成，其避免了与传统的UV光介导的方法有关的缺点。可见光介导的合成使用普通的玻璃器皿和简单的家用灯泡，而不会竞争性地形成[2 + 2]环加合物，区域异构体或过氧化产物苯并[ g ]过二甲苯3。初步结果表明，通过使用连续流动策略可以显着减少反应时间。

  DOI：

  10.1021/ol300983b

文献信息

• Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition-Metal Catalyzed Cycloisomerization Reactions
  作者：Victor Mamane、Peter Hannen、Alois Fürstner

  DOI：10.1002/chem.200400220

  日期：2004.9.20

  Readily available biphenyl derivatives containing an alkyne unit at one of their ortho-positions are converted into substituted phenanthrenes on exposure to catalytic amounts of either PtCl2, AuCl, AuCl3, GaCl3 or InCl3 in toluene. This 6-endo-dig cyclization likely proceeds through initial pi-complexation of the alkyne unit followed by interception of the resulting eta2-metal species by the adjacent

  在暴露于催化量的甲苯中的PtCl2，AuCl，AuCl3，GaCl3或InCl3时，容易获得的在邻位之一含有炔单元的联苯衍生物会转化为取代的菲。这种6-endo-dig环化反应可能是通过炔烃单元的最初pi络合反应进行，然后被相邻的芳烃环截获所得的eta2-金属。该反应固有地是模块化的，从而允许实质性的结构变化并允许在菲产物的任何位点上引入取代基。此外，它容易扩展到杂环系列，例如制备苯并吲哚，苯并咔唑，萘噻吩以及桥头氮杂环如吡咯并[1,2-a]喹啉。根据选择的催化剂，带有卤代炔单元的联芳基可以转化为相应的10-卤菲或异构体的9-卤菲。在后一种情况下，最好以金属亚乙烯基作为反应性中间体来解释伴随的1，2-卤化物移位。通过一系列与抗癌药康布雷他汀A-4的近亲相接的多加氧菲的全合成，以及阿波啡碱生物碱O-的全合成，可以说明这种制备多环芳烃的新方法的范围。甲基-脱氢异piline及其天然对称的二聚体
• Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes
  作者：Ming Chen、Xinxin Zhao、Chao Yang、Yanpei Wang、Wujiong Xia

  DOI：10.1039/c7ra00193b

  日期：——

  Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C–C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor

  本文报道了对3-芳基-N-（芳基磺酰基）-丙酰胺的光化学行为的进一步了解，这提供了一种直接途径来获得有意义的菲。机理研究表明，该过程涉及芳基迁移，CC偶联，1，3-氢转移，脱磺酰化和消除。此外，该协议允许使用流动反应器进行规模放大。
• Radical cyclisations to arenes for the synthesis of phenanthrenes
  作者：David C. Harrowven、Michael I.T. Nunn、David R. Fenwick

  DOI：10.1016/s0040-4039(02)00505-1

  日期：2002.4

  6-exo/endo-Trig intramolecular additions of aryl radicals to electron-rich, unsubstituted and electron-deficient arenes have all been shown to proceed efficiently to give the corresponding phenanthrenes in high yield.

  已经证明向富电子，未取代和缺电子的芳烃的芳基的6- exo / endo- trig分子内加成有效地进行，从而以高收率得到相应的菲。
• TOLL LIKE RECEPTOR (TLR) SIGNALING ANTAGONIST
  申请人：Upadhyay Shakti

  公开号：US20090215908A1

  公开（公告）日：2009-08-27

  The present invention relates to novel synthetic toll like receptor antagonist. The present invention in particular provides compounds, methods and compositions for specifically inhibiting immune stimulation involving TLR ligands, especially TLR-4. The compounds are potentially useful in treatment of inflammation, autoimmunity, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer and immunodeficiency.

  本发明涉及新型合成的Toll样受体拮抗剂。本发明特别提供了一种针对TLR配体特异性抑制免疫刺激的化合物、方法和组合物，尤其是针对TLR-4。这些化合物在治疗炎症、自身免疫、过敏、哮喘、移植排斥、移植物抗宿主病、感染、败血症、癌症和免疫缺陷方面具有潜在的用途。
• Exploiting the π-Acceptor Properties of Carbene-Stabilized Phosphorus Centered Trications [L₃P] ³⁺: Applications in Pt(II) Catalysis
  作者：Javier Carreras、Mahendra Patil、Walter Thiel、Manuel Alcarazo

  DOI：10.1021/ja306947m

  日期：2012.10.10

  Reaction of tris(dimethylaminocyclopropenium) substituted phosphine 1 with K2PtCl4 afforded the bench stable complex 3 which upon treatment with Ag[CB11H6Cl6] turned out to be an excellent catalyst for the transformation of a variety of ortho-biaryl substituted alkynes into polycyclic homo- and heteroarenes of different size, shape, and curvature through a 6-endo-dig cyclization. This constitutes the first example ever reported of using a P-1-centered trication as ligand in catalysis. The strong pi-acceptor character of 1 that derives from its three positive charges substantially increases the intrinsic pi-acidity of Pt in complex 1.PtCl2 and dramatically enhances its ability to activate pi-systems toward nucleophilic attack. As a consequence, a remarkable acceleration of the model transformation is observed when compared with other classical pi-acceptor ligands such as P(OPh)(3) or P(C6F5)(3). Moreover, the employment of 1 as ligand also expands the scope of this reaction to previously inaccessible substitution patterns. Kinetic studies and deuterium labeling experiments as well as density functional theory (DFT) calculations were performed in order to explain these findings.