4-benzyloxy-3a,4,5,9b-tetrahydro-3H-cyclopentaquinoline

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzyloxy-3a,4,5,9b-tetrahydro-3H-cyclopentaquinoline
• 英文别名: 4-benzoyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline；[(3aR,4S,9bS)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-4-yl]-phenylmethanone
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: GUZWMZFOSZGWJX-KYJSFNMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯基丙醇水合物 、 环戊二烯 、 苯胺 在 potassium hydrogensulfate 作用下， 以 甲醇 为溶剂， 反应 1.25h， 以52%的产率得到4-benzyloxy-3a,4,5,9b-tetrahydro-3H-cyclopentaquinoline
  参考文献：
  名称：

  硫酸氢钾催化的杂二烯的逆电子需求 Diels-Alder 反应：吡喃苯并吡喃、呋喃苯并吡喃和四氢喹啉衍生物的非对映选择性一锅法合成

  摘要：

  硫酸氢钾催化醛、苯胺和富电子双烯体如二氢吡喃、二氢呋喃、乙基乙烯基醚和环戊二烯的一锅三组分偶联。对于邻羟基苯甲醛，反应可能通过形成邻醌甲基化物中间体进行，该中间体随后与环状和非环状烯醇醚进行环加成反应，形成相应的色烷。然而，在没有邻羟基的苯甲醛的情况下，形成的亚胺充当杂二烯并导致形成四氢喹啉。

  DOI：

  10.1055/s-2004-822332

文献信息

• Lanthanide Triflate Catalyzed Imino Diels-Alder Reactions; Convenient Syntheses of Pyridine and Quinoline Derivatives
  作者：Shū Kobayashi、Haruro Ishitani、Satoshi Nagayama

  DOI：10.1055/s-1995-4066

  日期：1995.9

  Lanthanide triflate catalyzed imino Diels-Alder reactions of imines with dienes or alkenes have been developed. A new group of Lewis acids, lanthanide triflates, are quite effective for the catalytic activation of imines. Unique reactivities of imines which work as both dienophiles and azadienes under certain conditions have been revealed. Three-component coupling reactions between aldehydes, amines, and dienes or alkenes were successfully carried out by using lanthanide triflate as a catalyst to afford pyridine and quinoline derivatives in high yields. The Lewis acid catalysts were stable and kept their activity even in the presence of water and amines. A stepwise reaction mechanism for these reactions is suggested from the experimental results.

  已开发了铈三氟甲磺酸盐催化的亚胺与二烯或烯烃的亚胺Diels-Alder反应。新一类路易斯酸，即铈三氟甲磺酸盐，在催化亚胺的活化方面非常有效。已揭示出亚胺在某些条件下同时作为二烯亲和体和氮烯体的独特反应性。通过使用铈三氟甲磺酸盐作为催化剂，成功进行了醛、胺与二烯或烯烃之间的三组分偶联反应，得到高产率的吡啶和喹啉衍生物。这些路易斯酸催化剂在水和胺存在的情况下依然保持稳定性和活性。根据实验结果，提出了这些反应的逐步反应机理。
• Triphenyl phosphonium perchlorate—an efficient catalyst for the imino Diels–Alder reaction of imines with electron rich dienophiles. Synthesis of pyranoquinoline, furoquinoline and phenanthridine derivatives
  作者：Rajagopal Nagarajan、Sundararajan Chitra、Paramasivan T Perumal

  DOI：10.1016/s0040-4020(01)00185-5

  日期：2001.4

  Triphenyl phosphonium perchlorate (TPP) is found to be an efficient catalyst for the imino Diels-Alder reaction of aldimines with cyclopentadiene and 3,4-dihydro-2H-pyran is reported for the first time. One pot synthesis of furoquinoline, cyclopentaquinolines and phenanthridine catalysed by TPP is also reported in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A New Methodology for Combinatorial Synthesis. Preparation of Diverse Quinoline Derivatives Using a Novel Polymer-Supported Scandium Catalyst
  作者：Shū Kobayashi、Satoshi Nagayama

  DOI：10.1021/ja961062l

  日期：1996.1.1
• Inverse Electron Demand Diels-Alder Reactions of Heterodienes Catalyzed by Potassium Hydrogen Sulfate: Diastereoselective, One-Pot Synthesis of Pyranobenzopyrans, Furanobenzopyrans and Tetrahydroquinolines Derivatives
  作者：Paramasivan T. Perumal、R. Senthil Kumar、Rajagopal Nagarajan

  DOI：10.1055/s-2004-822332

  日期：——

  Potassium hydrogen sulfate catalyzes the one-pot three components coupling of aldehydes, anilines, and electron rich dienophiles such as dihydropyran, dihydrofuran, ethyl vinylether, and cyclopentadiene. With o-hydroxybenzaldehyde, the reaction probably proceeds through the formation of o-quinonemethide intermediate, which subsequently undergoes cycloaddition with cyclic and acyclic enol ethers leading

  硫酸氢钾催化醛、苯胺和富电子双烯体如二氢吡喃、二氢呋喃、乙基乙烯基醚和环戊二烯的一锅三组分偶联。对于邻羟基苯甲醛，反应可能通过形成邻醌甲基化物中间体进行，该中间体随后与环状和非环状烯醇醚进行环加成反应，形成相应的色烷。然而，在没有邻羟基的苯甲醛的情况下，形成的亚胺充当杂二烯并导致形成四氢喹啉。