5,8-dimethoxycyclopentaquinoline | 131251-73-5

• 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: 5,8-dimethoxycyclopentaquinoline
• 英文别名: 5,8-dimethoxy-2,3-dihydro-1H-cyclopenta[b]quinoline
• CAS: 131251-73-5
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: YQASFYJBVKSAKX-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  398.2±37.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)
• 溶解度：
  29 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,8-dimethoxycyclopentaquinoline 在 吡啶-2,6-二羧酸 n-氧化物 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以54%的产率得到cyclopentaquinoline-5,8-quinone
  参考文献：
  名称：

  Heteroaromatic fused derivatives of tetracyclo[6.3.0.04,11.O5,9]undecane

  摘要：

  A series of rigid syn-orthocyclophanes is prepared by the Friedlander condensation of appropriate o-amino-benzaldehyde derivatives with tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione. The reaction may proceed in a stepwise fashion so that unsymmetrical layered compounds can be prepared. These species can be further elaborated by oxidation to quinolinequinones or N-oxides and quaternization to quinolinium salts. Molecular mechanics calculations agree closely with X-ray analysis in describing the structural properties of these cyclophanes. Analysis of the H-1 NMR and UV spectra as well as the reduction potentials of these molecules support a moderate electronic interaction between the decks. Initial investigations regarding their ability to serve as cleft-type hosts are described.

  DOI：

  10.1021/jo00004a029
• 作为产物：
  描述：

  2-溴环戊烯-1-甲醛 在 tris(dibenzylideneacetone)dipalladium (0) 、 potassium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 5,8-dimethoxycyclopentaquinoline
  参考文献：
  名称：

  Chemoselective arylamination of β-bromovinylaldehydes followed by acid catalyzed cyclization: a general method for polycyclic quinolines

  摘要：

  A synthesis of polycyclic quinolines is described via palladium-catalyzed chemoselective arylamination of beta-bromovinylaldehydes with aromatic amines followed by acid catalyzed cyclization. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.111

文献信息

• Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes
  作者：Mark Austin、Oliver J. Egan、Raymond Tully、Albert C. Pratt

  DOI：10.1039/b711620a

  日期：——

  resulting in 7-substituted products. 2-Furylmethylene and 2-thienylmethylene analogues yield annulated furo- and thieno-[2,3e]pyridines respectively. Sequential E- to Z-benzylidene group isomerisation and six pi-electron cyclisation steps result in formation of a short-lived dihydroquinoline intermediate which spontaneously aromatises by elimination of an alcohol or acetic acid. For 2-benzylidenecyclopentanone

  在甲醇中辐照取代的2-亚苄基环戊酮的O-烷基和O-乙酰肟，可以方便地合成烷基，烷氧基，羟基，乙酰氧基，氨基，二甲基氨基和苯并取代的环喹啉。对位取代基可生成6位取代的2,3-二氢-1H-环戊基[b]喹啉，其中8位取代的产物可从邻位取代的起始原料中获得。间位取代的前体的反应是高度区域选择性的，烷基取代基导致5-取代的2,3-二氢-1H-环戊[b]喹啉和更强的供电子取代基，通常产生7-取代的产物。2-呋喃基亚甲基和2-噻吩基亚甲基类似物分别产生环呋喃基和噻吩并[2,3e]吡啶。依次的E-到Z-亚苄基异构化和六个π电子环化步骤导致形成短寿命的二氢喹啉中间体，该中间体通过消除醇或乙酸而自发芳香化。对于2-亚苄基环戊酮O-烯丙基肟，两个步骤均涉及单重态激发态。
• LIM, JEAN-LUC;CHIRAYIL, SARA;THUMMEL, RANDOLPH P., J. ORG. CHEM., 56,(1991) N, C. 1492-1500
  作者：LIM, JEAN-LUC、CHIRAYIL, SARA、THUMMEL, RANDOLPH P.

  DOI：——

  日期：——
• Heteroaromatic fused derivatives of tetracyclo[6.3.0.04,11.O5,9]undecane
  作者：Jean Luc Lim、Sara Chirayil、Randolph P. Thummel

  DOI：10.1021/jo00004a029

  日期：1991.2

  A series of rigid syn-orthocyclophanes is prepared by the Friedlander condensation of appropriate o-amino-benzaldehyde derivatives with tetracyclo[6.3.0.0(4,11).0(5,9)]undecane-2,7-dione. The reaction may proceed in a stepwise fashion so that unsymmetrical layered compounds can be prepared. These species can be further elaborated by oxidation to quinolinequinones or N-oxides and quaternization to quinolinium salts. Molecular mechanics calculations agree closely with X-ray analysis in describing the structural properties of these cyclophanes. Analysis of the H-1 NMR and UV spectra as well as the reduction potentials of these molecules support a moderate electronic interaction between the decks. Initial investigations regarding their ability to serve as cleft-type hosts are described.
• Chemoselective arylamination of β-bromovinylaldehydes followed by acid catalyzed cyclization: a general method for polycyclic quinolines
  作者：Surajit Some、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2007.05.111

  日期：2007.7

  A synthesis of polycyclic quinolines is described via palladium-catalyzed chemoselective arylamination of beta-bromovinylaldehydes with aromatic amines followed by acid catalyzed cyclization. (C) 2007 Elsevier Ltd. All rights reserved.