4-ethoxy-2-phenyl-1,2,3,4-tetrahydroquinoline | 5278-41-1

• 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
• 英文名称: 4-ethoxy-2-phenyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 4-Ethoxy-2-phenyl-1,2,3,4-tetrahydro-chinolin；2-Phenyl-4-ethoxy-1,2,3,4-tetrahydrochinolin
• CAS: 5278-41-1
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: DHZUCMCOXHWWHK-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  158-159 °C(Press: 1.5 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙烯基乙醚 、 N-(phenylmethylene)benzenamine 在 bismuth(lll) trifluoromethanesulfonate 、 水 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以92%的产率得到4-ethoxy-2-phenyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Laurent-Robert; Garrigues; Dubac, Synlett, 2000, # 8, p. 1160 - 1162

  摘要：

  DOI：

文献信息

• Imino-Diels–Alder and imino-aldol reactions catalyzed by samarium diiodide
  作者：Jacqueline Collin、Nada Jaber、Marie Isabelle Lannou

  DOI：10.1016/s0040-4039(01)01581-7

  日期：2001.10

  In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones.

  在二氯甲烷中催化量的二碘化sa存在下，芳族亚胺与Danishefsky二烯反应形成高产率的四氢吡啶-4-酮。在相同条件下，各种亚氨基-羟醛反应可得到β-氨基酯或β-氨基酮。
• Facile Synthesis of Tetrahydroquinolines and Julolidines through ­Multicomponent Reaction
  作者：Julien Legros、Benoit Crousse、Michèle Ourévitch、Danièle Bonnet-Delpon

  DOI：10.1055/s-2006-947360

  日期：2006.8

  trifluoroethanol (TFE) through an aza-Diels-Alder reaction (Povarov reaction) to afford the corresponding substituted tetrahydroquinolines. This reaction occurs, without any catalyst, under sequential three-component conditions, allowing thus the use of aliphatic aldehydes. In the presence of formaldehyde and an excess of dienophile, the product undergoes a second Povarov reaction affording new julolidine

  醛、苯胺和烯醇醚在三氟乙醇 (TFE) 中通过 aza-Diels-Alder 反应（Povarov 反应）反应，得到相应的取代四氢喹啉。该反应在没有任何催化剂的情况下在连续的三组分条件下发生，因此允许使用脂肪醛。在甲醛和过量亲二烯体的存在下，产物进行第二次波瓦洛夫反应，得到新的聚苯胺衍生物。
• 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。
• Reexamining Povarov Reaction’s Scope and Limitation in the Generation of HCV-NS4A Peptidomimetics
  作者：Maan T. Khayat、Abdelsattar M. Omar、Mahmoud A. Elfaky、Yosra A. Muhammad、Elaf A. Felemban、Khalid M. El-Say、Moustafa E. El-Araby

  DOI：10.1155/2022/8181543

  日期：2022.2.10

  mimics that cover the region between residues Ile-25′ to Arg-28′. The synthetic plan featured the Povarov reaction as an efficient strategy to construct the 1,7-naphthyridine core. Although this reaction has been reported in many literatures, critical assessments for its scope and limitations are scarce. In our work, we found that Povarov was extremely sensitive to alkene and aldehyde reactants. Moreover

  慢性丙型肝炎是一种全球健康威胁和无声杀手。尽管在预防和治疗这种疾病方面取得了重大进展，但研究仍在继续发现新的直接抗病毒药物 (DAA)，尤其是针对新靶点的药物。我们的研究旨在利用 NS4A 结合位点开发丙型肝炎病毒 (HCV) NS3 蛋白酶的拟肽抑制剂。在以前的报告中，我们可以提供肽和非肽 NS3/4A 抑制剂对该位点的可调性的证据。在本报告中，我们使用基于结构的技术设计 1,2,3,4-四氢-1,7-萘啶衍生物作为 NS4A 核心模拟物，覆盖残基 Ile-25' 到 Arg-28' 之间的区域。该合成计划将波瓦罗夫反应作为构建 1,7-萘啶核的有效策略。尽管许多文献都报道了这种反应，但对其范围和局限性的批判性评估却很少。在我们的工作中，我们发现波瓦罗夫对烯烃和醛反应物极为敏感。此外，使用吡啶胺不如苯胺成功。最引人注目的结果是化合物在纯化和储存过程中缺乏稳定性。在稳定性问题中幸存下来的四种化合物
• New Findings on the Cerium(IV) Ammonium Nitrate Catalyzed Povarov Reaction: Stereoselective Synthesis of 4-Alkoxy-2-aryl-1,2,3,4-tetrahydro­quinoline Derivatives
  作者：J. Menéndez、Vellaisamy Sridharan、Carmen Avendaño

  DOI：10.1055/s-2008-1032126

  日期：——

  Cerium(IV) ammonium nitrate catalyzes the three-component, imino Diels-Alder (Povarov) reaction between anilines, aromatic aldehydes, and acyclic vinyl ethers, giving cis-4-alkoxy-2-aryl-1,2,3,4-tetrahydroquinolines with almost complete diastereoselectivity. The corresponding reaction starting from cyclic vinyl ethers gave the two possible diastereomers, with the endo-compound as the major product. This stereochemical outcome is explained through a stepwise mechanism for the imino Diels-Alder reaction, and this mechanism was subsequently proved by trapping the putative oxonium intermediate in the presence of ethanol.

  硝酸铈（IV）铵催化苯胺、芳香醛和无环乙烯醚之间的三组分亚胺型迪尔斯-阿尔德（波瓦洛夫）反应，生成具有几乎完全非对映选择性顺式-4-烷氧基-2-芳基-1,2,3,4-四氢喹啉。从环状乙烯醚开始的相应反应产生了两种可能的非对映异构体，内型化合物为主要产物。通过亚胺型迪尔斯-阿尔德反应的逐步机制解释了这种立体化学结果，随后在乙醇存在下捕获推测的氧离子中间体证实了这一机制。