4-phenyl-2,3-dihydrofuro[3,2-c]quinoline | 248953-10-8

• 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: 4-phenyl-2,3-dihydrofuro[3,2-c]quinoline
• CAS: 248953-10-8
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: MOCGSMMXRRQYRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-2,3-dihydrofuro[3,2-c]quinoline 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 以48%的产率得到2-((2S*,3S*)-2-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)ethan-1-ol
  参考文献：
  名称：

  路易斯酸促进炔烃的氧离子驱动的碳氨化反应，以合成4-烷氧基喹啉

  摘要：

  路易斯酸介导的多段偶联级联反应是设计用于通过含氧离子触发的炔烃碳氨化序列（涉及C–C和C–N键的形成）来合成密集取代的4-烷氧基喹啉。还可以使用这种快速，操作简单，高收率，化学选择性和功能基团耐受的方法获得环醚稠合喹啉。该方法的多功能性和实用性通过所获得产品的后功能化及其在有效药物分子合成中的应用来证明。

  DOI：

  10.1021/acs.joc.6b02896
• 作为产物：
  描述：

  N-(diphenylmethylene)-2-iodoaniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 4-phenyl-2,3-dihydrofuro[3,2-c]quinoline
  参考文献：
  名称：

  Scaffold-Divergent Synthesis of Ring-Fused Indoles, Quinolines, and Quinolones via Iodonium-Induced Reaction Cascades

  摘要：

  N-(2-lodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.

  DOI：

  10.1021/jo400125p

文献信息

• Silver-catalyzed tandem 5- and 6-<i>endo</i>-cyclizations <i>via</i> concomitant yne-ol-imine activation: selective entry to 2-aryldihydrofuroquinolines
  作者：Swastik Karmakar、Prasanta Das、Sandip Kundu

  DOI：10.1039/d1nj02643g

  日期：——

  Ag(i)-catalyzed domino imination-intramolecular bi-heterocyclization-aromatization cascade has been developed to construct 2-aryldihydrofuroquinolines from aldehyde and unprotected 4-(2-aminophenyl)but-3-yn-1-ol via tandem 5-endo-dig and 6-endo-trig cyclization.

  已开发出Ag（i）催化的多米诺亚胺化-分子内双杂环化-芳构化级联反应，用于从醛和未保护的4-(2-氨基苯基)丁-3-炔-1-醇构建2-芳基二氢呋喃喹啉，通过串联5-内端挖和6-内端挖环化。
• Silver‐Catalyzed Carbocyclization of Azide‐Tethered Alkynes: Expeditious Synthesis of Polysubstituted Quinolines
  作者：Xinfang Xu、Han Su、Ming Bao、Jingjing Huang、Lihua Qiu

  DOI：10.1002/adsc.201801425

  日期：——

  A silver‐catalyzed carbocyclization of azide‐tethered alkynes has been developed for the synthesis of polysubstituted quinolines in good to high yields. Mechanistic studies indicate that this reaction is initiated by a silver‐catalyzed 6‐endo‐dig azide‐yne cyclization, followed by a formal R−X (X=Cl, Br, or I) insertion with external halide through a ylide intermediate. The salient features of this

  已开发出一种银催化的叠氮化物束缚炔烃的碳环化反应，以高产率到高产率合成多取代的喹啉。机理研究表明，该反应是由银催化的6-内切-叠氮叠氮炔环化反应引发的，随后是正式的RX（X = Cl，Br或I）与外部卤化物通过叶立德中间体插入。该反应的显着特征包括容易获得的材料，廉价的银催化剂，温和的反应条件，良好的官能团耐受性和易于进一步转化的特点。
• Acid‐Mediated Condensation of 2‐Aminoaryl Cyclopropyl Ketones with Aldehydes for the Synthesis of 2,3‐Dihydrofuro[3,2‐c]quinolines
  作者：Wenbo Cai、Cong Zhang、Xin Wang、Chuanjun Song

  DOI：10.1002/adsc.202400263

  日期：——

  A method for the synthesis of 2,3-dihydrofuro[3,2-c]quinolines via TfOH or TMSOTf mediated condensation of 2-aminoaryl cyclopropyl ketones with aldehydes has been developed. The reaction proceeds under transition metal or halogen free conditions, giving access to the target molecules in 27-90% isolated yields. Mechanistic study indicates that the reaction sequence involves imine formation, intramolecular

  开发了一种通过 TfOH 或 TMSOTf 介导的 2-氨基芳基环丙基酮与醛的缩合合成 2,3-二氢呋喃并[3,2-c]喹啉的方法。该反应在无过渡金属或卤素的条件下进行，以 27-90% 的分离产率获得目标分子。机理研究表明，反应顺序涉及亚胺形成、分子内曼尼希缩合、Cloke-Wilson 重排和自动氧化。
• Ru-Catalyzed Synthesis of Dihydrofuroquinolines from Azido-cyclopropyl Ketones
  作者：Weijun Yang、Lijun Xu、Zhengkai Chen、Lili Zhang、Maozhong Miao、Hongjun Ren

  DOI：10.1021/ol400223d

  日期：2013.3.15

  An efficient Ru-catalyzed synthesis of dihydrofuroquinolines from azido-cyclopropyl ketones via the reduction-cyclization-rearrangement process is reported. A plausible reaction mechanism for this process is depicted. Additionally, when the reaction was carried out under H-2 (1 atm) In the presence of Pd/C, 4-quinolones were obtained in excellent yields.
• Alternating Iodonium-Mediated Reaction Cascades Giving Indole- And Quinoline-Containing Polycycles
  作者：Rosliana Halim、Peter J. Scammells、Bernard L. Flynn

  DOI：10.1021/ol800202u

  日期：2008.5.1

  A simple two-step convergent protocol gives direct access to synthetic intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS in CH(2)Cl(2) to induce novel iodonium mediated domino reaction cascade, which provides direct access to ring-fused indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.