4-phenyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid | 122059-86-3

• 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-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid
• 英文别名: (3aS,4R,9bR)-4-phenyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid
• CAS: 122059-86-3
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: LKCVPAJAXLUURH-VKJFTORMSA-N

物化性质

• 熔点：
  206-207 °C
• 沸点：
  484.0±45.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为产物：
  描述：

  4-(α-benzylideneamino)benzoic acid 、 环戊二烯 在 草酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以75%的产率得到4-phenyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-8-carboxylic acid
  参考文献：
  名称：

  草酸二水合物催化的亚氨基-狄尔斯-阿尔德反应。四氢喹啉衍生物的合成

  摘要：

  发现二水草酸可催化由取代苯胺衍生的席夫碱与环戊二烯的亚氨基狄尔斯-阿尔德反应，导致以中等产率形成四氢喹啉衍生物。

  DOI：

  10.1081/scc-100103994

文献信息

• 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。
• UREA NITRATE CATALYZED IMINO DIELS-ALDER REACTIONS: SYNTHESIS OF CYCLOPENTAQUINOLINES, PYRANOQUINOLINES, AND FUROQUINOLINE DERIVATIVES
  作者：Marimuthu Anniyappan、Rajagopal Nagarajan、Paramasivan T. Perumal

  DOI：10.1081/scc-120001514

  日期：2002.1.1

  ABSTRACT Urea nitrate is found to be an efficient catalyst for the imino Diels-Alder reaction of aldimines with cyclopentadiene, 3,4-dihydropyran and dihydrofuran is reported for the first time. One pot synthesis of cyclopentaquinolines from benzaldehyde, aromatic amines with cyclopentadiene catalyzed by urea nitrate is also reported.

  摘要 硝酸尿素被发现是醛亚胺与环戊二烯、3,4-二氢吡喃和二氢呋喃的亚氨基Diels-Alder 反应的有效催化剂，这是首次报道。还报道了由苯甲醛、芳香胺与硝酸尿素催化的环戊二烯一锅合成环戊喹啉。
• 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.
• Role reversal in the cyclocondensation of cyclopentadiene with heterodienophiles derived from aryl amines and aldehydes: Synthesis of novel tetrahydroquinolines
  作者：Paul A. Grieco、Ali Bahsas

  DOI：10.1016/s0040-4039(00)82208-x

  日期：1988.1
• Nagarajan, Rajagopal; Magesh, Chinnan J.; Perumal, Paramasivan T., Synthesis, 2004, # 1, p. 69 - 74
  作者：Nagarajan, Rajagopal、Magesh, Chinnan J.、Perumal, Paramasivan T.

  DOI：——

  日期：——