2-氯吖啶 | 1207-96-1

• 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
• 中文名称: 2-氯吖啶
• 英文名称: 2-chloroacridine
• 英文别名: 2-Chlor-acridin
• CAS: 1207-96-1
• 化学式: C₁₃H₈ClN
• 分子量: 213.666
• InChiKey: NDAXYJIUSLEMIY-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C
• 沸点：
  379.4±15.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-chloro-2-(hydroxy(phenyl)methyl)-1-(4-methylphenylsulfonamido)benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 2-氯吖啶
  参考文献：
  名称：

  Diels–Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives

  摘要：

  N-Tosyl- and N-alkylidene-sulfonyl substituted 1,4-dihydro-2N-3,1-benzoxazin-2-ones 2c-g easily undergo thermal carbon dioxide extrusion leading to the aza-ortho-xylylenes 3c-g, The intermediates 3c,d can be trapped by electron-poor ethylenic and acetylenic dienophiles, giving tetrahydroquinoline and quinoline derivatives, The reactions of 2c with non-symmetrical dienophiles are completely regioselective, N-Alkylidenesulfonyl substituted aza-ortho-xylylenes 3f-g undergo intramolecular Diels-Alder reactions leading to the tricyclic compounds 10 and 11, while the aza-ortho-xylylene generated from 4-(hex-5-enyl)-N-(4-methylphenylsulfonyl)-1,4-tetrahydro-2N-3,1-benzoxazin-2-one undergoes a [1,5] hydrogen shift leading to N-[2-(1E)-hepta-1,6-dien-1-ylphenyl]-4-methylbenzenesulfonamide.

  DOI：

  10.1039/p19960001809

文献信息

• Cu-Catalyzed Cascade Reaction of Isoxazoles with Diaryliodonium Salts for the Synthesis of Acridines
  作者：Shangrong Zhu、Xuechen Lu、Qiuneng Xu、Jian Li、Shenghu Yan

  DOI：10.2174/1570178617666200225125427

  日期：2020.12.8

  A straightforward and efficient synthesis of acridine derivatives via a copper-catalyzed cascade reaction among isoxazoles and diaryliodonium salts is achieved. Various mono-, multi-substituted and 9-substituted acridine derivatives could be obtained in moderate to good yields. The process has gone through tandem double arylation and Friedel-Crafts reactions.

  通过异恶唑和二芳基碘鎓盐之间的铜催化的级联反应，可以直接有效地合成a啶衍生物。可以以中等至良好的产率获得各种单，多取代和9-取代的cr啶衍生物。该过程经历了串联双芳基化和Friedel-Crafts反应。
• Rh(<scp>iii</scp>)-Catalyzed bilateral cyclization of aldehydes with nitrosos toward unsymmetrical acridines proceeding with C–H functionalization enabled by a transient directing group
  作者：Weiming Hu、Qingheng Zheng、Song Sun、Jiang Cheng

  DOI：10.1039/c7cc03006a

  日期：——

  A Rh(III)-catalyzed bilateral cyclization was developed for the efficient construction of acridines proceeding with C–H functionalization whereby in situ formation and removal of an imino transient directing group in the presence of catalytic amount of BnNH2 are achieved. In this transformation, a sequential Rh(III)-catalyzed C–H amination, cyclization, and aromatization process was involved.

  开发了Rh（III）催化的双环环化反应，可有效构建–啶并进行C–H官能化，从而在催化量的BnNH 2存在下原位形成和去除亚氨基瞬态导向基团。在此转化过程中，涉及到了连续的Rh（III）催化的CH–H胺化，环化和芳构化过程。
• Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol
  作者：Ting-Jun Wang、Wen-Wen Chen、Yi Li、Ming-Hua Xu

  DOI：10.1039/c5ob00755k

  日期：——

  A facile and efficient approach for the synthesis of a variety of acridines via the tandem coupling/cyclization of substituted 2-bromobenzaldehydes and anilines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Pd2(dba)3 and diphosphine ligand dppf, providing a broad range of substituted acridines in good to excellent yields (up to 99%). The Lewis acid

  描述了通过取代的2-溴苯甲醛和苯胺的串联偶联/环化来合成各种cr啶的简便有效的方法。在催化量的Pd 2（dba）3和二膦配体dppf的存在下，可以轻松完成反应，从而以良好至极佳的收率（高达99％）提供广泛的取代cr啶。需要路易斯酸AlCl 3来促进较少电子富集的苯胺的环化。
• Rh(III)-catalyzed synthesis of unsymmetrical acridines from aldehydes and azides using transient directing strategy in biomass-derived <font>γ</font>-valerolactone
  作者：Jun Shen、Xi Liu、Liang Wang、Qun Chen、Mingyang He

  DOI：10.1080/00397911.2018.1448418

  日期：2018.6.3

  ABSTRACT An Rh(III)-catalyzed synthesis of unsymmetrical acridines from aldehydes and azides through bilateral cyclization process in biomass-derived γ-valerolactone has been developed. The in situ-generated imino directing group (DG) from aldehyde and catalytic amount of BnNH2 worked as a transient directing group, thereby no additional steps were required for installation and removal of the DG. A

  摘要 已经开发了在生物质衍生的 γ-戊内酯中通过双环化过程从醛和叠氮化物合成不对称吖啶的 Rh(III)。由醛和催化量的 BnNH2 原位生成的亚氨基导向基团 (DG) 作为瞬态导向基团，因此不需要额外的步骤来安装和去除 DG。一系列官能团具有良好的耐受性，以良好到极好的产率提供所需的产品。也实现了产物的克级合成。图形概要
• Synthesis of acridines <i>via</i> copper-catalyzed amination/annulation cascades between arylboronic acids and anthranils
  作者：Yuge Li、Liang Xu、Yu Wei

  DOI：10.1039/d2ob01705a

  日期：——

  Copper-catalyzed tandem cyclization reactions between arylboronic acids and anthranils have been established, providing new approaches for one-pot assembly of azacycle acridines. This one-pot protocol features simple operation, precious-metal-free conditions and good functional group compatibility, thus providing an efficient approach for the synthesis of a variety of acridines in moderate to good

  已经建立了铜催化的芳基硼酸和邻氨基苯甲酸之间的串联环化反应，为氮杂环吖啶的一锅法组装提供了新途径。该一锅法操作简单，无贵金属条件，官能团相容性好，为多种吖啶的中等收率合成提供了一种有效途径。