6-pentylphenanthridine | 16171-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-pentylphenanthridine
• 英文别名: Phenanthridine, 6-pentyl-
• CAS: 16171-51-0
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: VGCYIFWXAIGWNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  181 °C(Press: 1 Torr)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-([1,1'-biphenyl]-2-yl)hexan-1-one 在 三氟甲磺酸 、 叠氮基三甲基硅烷 作用下， 以 三氟乙酸 为溶剂， 反应 12.0h， 以81%的产率得到6-pentylphenanthridine
  参考文献：
  名称：

  Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines

  摘要：

  An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.

  DOI：

  10.1021/acs.orglett.5b00797

文献信息

• Selective Synthesis of Dihydrophenanthridine and Phenanthridine Derivatives from the Cascade Reactions of <i>o</i>-Arylanilines with Alkynoates through C–H/N–H/C–C Bond Cleavage
  作者：Yuanshuang Xu、Caiyun Yu、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.joc.1c00256

  日期：2021.4.16

  unprecedented selective synthesis of dihydrophenanthridine and phenanthridine derivatives through the cascade reactions of 2-arylanilines with alkynoates is presented. Mechanistic studies showed that the formation of the dihydrophenanthridine scaffold involves an initial C(sp2)–H alkenylation of 2-arylaniline with alkynoate followed by an intramolecular aza-Michael addition. When this reaction is carried out

  在本文中，提出了通过2-芳基苯胺与链烷酸酯的级联反应对二氢菲啶和菲啶衍生物进行空前的选择性合成。机理研究表明，二氢菲啶骨架的形成涉及初始C（sp 2）–炔基酸将2-芳基苯胺的H烯基化，然后进行分子内氮杂-Michael加成反应。当该反应在高温下进行时，原位形成的取代的二氢菲啶很容易发生逆曼尼希型反应，通过CC键断裂得到相应的菲啶。与文献方法相比，该新颖方案具有诸如容易获得的具有游离氨基的底物，药学上特权的产品，廉价的催化剂以及方便地可控制的选择性的优点。
• Rapid synthesis of polysubstituted phenanthridines from simple aliphatic/aromatic nitriles and iodo arenes <i>via</i> Pd(<scp>ii</scp>) catalyzed domino C–C/C–C/C–N bond formation
  作者：Yogesh Jaiswal、Yogesh Kumar、Jagannath Pal、Ranga Subramanian、Amit Kumar

  DOI：10.1039/c8cc03556c

  日期：——

  An efficient and straightforward method has been developed for the synthesis of polysubstituted phenanthridines from simple aryl iodides and alkyl/aryl nitriles via the palladium-catalyzed nucleophilic addition of aryl iodides to nitriles followed by cascade formation of C–C and C–N bonds viz. in situ generated imine directed sequential two fold C–H activation.

  已开发出一种有效，简单的方法，可通过钯催化的芳基碘化物向腈中的亲核加成反应，由简单的芳基碘化物和烷基/芳基腈合成多取代的菲啶，然后级联形成C–C和C–N键。原位产生的亚胺定向连续2次C–H活化。
• Unprecedented Hydrothermal Reaction of <i>O</i>-Phenylaniline and Related Derivatives with Cyclic Ketones. A Novel Approach to the Construction of Phenanthridine and Quinoline Ring Systems
  作者：Barun K. Mehta、Kazumichi Yanagisawa、Motoo Shiro、Hiyoshizo Kotsuki

  DOI：10.1021/ol0300120

  日期：2003.5.1

  [reaction: see text] A new method for synthesizing phenanthridine and its related compounds was developed using the condensation of o-phenylaniline and its homologues with cyclic ketones under hydrothermal conditions.

  [反应：见正文]在水热条件下，利用邻苯基苯胺及其同系物与环酮的缩合，开发了一种合成菲啶及其相关化合物的新方法。
• [EN] NOVEL HYDROXY-6-HETEROARYLPHENANTHRIDINES AND THEIR USE AS PDE4 INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS DE HYDROXY-6-HÉTÉROARYLPHÉNANTHRIDINE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PDE4
  申请人：ALTANA PHARMA AG

  公开号：WO2005085225A1

  公开（公告）日：2005-09-15

  Compounds of formula (I), in which R1 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, 2,2-difluoroethoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, R2 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, 2,2-difluoroethoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, or in which R1 and R2 together are a 1-2C-alkylenedioxy group, R3 is hydrogen or 1-4C-alkyl, R31 is hydrogen or 1-4C-alkyl, either, in a first embodiment (embodiment a) according to the present invention, R4 is -O-R41, in which R41 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-7C-alkylcarbonyl, or completely or predominantly fluorine-substituted 1-4C-alkyl, and R5 is hydrogen or 1-4C-alkyl, or, in a second embodiment (embodiment b) according to the present invention, R4 is hydrogen or 1-4C-alkyl, and R5 is -O-R51, in which R51 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-7C-alkylcarbonyl, or completely or predominantly fluorine-substituted 1-4C-alkyl, Har is optionally substituted by R6 and/or R7 and/or R8, and is a 5- to 10-membered monocylic or fused bicyclic unsaturated or partially saturated heteroaryl radical comprising 1 to 4 heteroatoms selected independently from the group consisting of oxygen, nitrogen and sulfur, are novel effective PDE4 inhibitors.

  公式（I）中的化合物，其中R1是羟基，1-4C-烷氧基，3-7C-环氧基，3-7C-环烷基甲氧基，2,2-二氟乙氧基，或完全或主要氟代的1-4C-烷氧基，R2是羟基，1-4C-烷氧基，3-7C-环氧基，3-7C-环烷基甲氧基，2,2-二氟乙氧基，或完全或主要氟代的1-4C-烷氧基，或者R1和R2一起是1-2C-烷二氧基基团，R3是氢或1-4C-烷基，R31是氢或1-4C-烷基，在本发明的第一实施例（实施例a）中，R4是-O-R41，其中R41是氢，1-4C-烷基，1-4C-烷氧基-1-4C-烷基，羟基-2-4C-烷基，1-7C-烷基羰基，或完全或主要氟代的1-4C-烷基，而R5是氢或1-4C-烷基，或者在本发明的第二实施例（实施例b）中，R4是氢或1-4C-烷基，而R5是-O-R51，其中R51是氢，1-4C-烷基，1-4C-烷氧基-1-4C-烷基，羟基-2-4C-烷基，1-7C-烷基羰基，或完全或主要氟代的1-4C-烷基，Har可选地由R6和/或R7和/或R8取代，并且是包含1至4个异原子（独立选择自氧、氮和硫组成的）的5-到10-成员单环或融合的双环不饱和或部分饱和杂环基团，是新颖的有效PDE4抑制剂。
• Novel Salts of 6-Heterocycle Substituted Hexahydrophenanthridine Derivatives
  申请人：Kautz Ulrich

  公开号：US20080194587A1

  公开（公告）日：2008-08-14

  The invention relates to salts of 6-heteroaryl substituted hexahydrophenanthridine PDE4-inhibiting compounds, which can be used in the pharmaceutical industry for the production of pharmaceutical compositions for use, e.g., in treatment of airway disorders.

  本发明涉及6-杂环芳基取代的六氢苯并三唑磷酸酯（PDE4）抑制剂化合物的盐，可用于制备制药组合物，例如用于治疗呼吸道疾病的制药组合物。