cis-5-(4-bromophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline

• 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: cis-5-(4-bromophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
• 英文别名: (4aS,5S,10bS)-5-(4-bromophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
• 化学式: C₁₈H₁₈BrNO
• 分子量: 344.251
• InChiKey: GBMXBGXKOREWBD-CGTJXYLNSA-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：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  对溴苯甲醛 以 乙腈 为溶剂， 生成 cis-5-(4-bromophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline 、 (4aS,5R,10bS)-5-(4-bromophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
  参考文献：
  名称：

  Kaur, Ramneet; Khajuria, Rajni; Saini, Yeshwinder, Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 1, p. 91 - 102

  摘要：

  DOI：

文献信息

• Proline triflate catalysed Diels–Alder reaction in the synthesis of tetrahydroquinoline derivatives
  作者：Jianjun Li、Jia Li、Weike Su

  DOI：10.3184/030823409x12474221035082

  日期：2009.8

  Proline triflate was found to catalyse efficiently the one-pot synthesis of 2H-pyranotetrahydroquinolines from aryl imines, and 3,4-dihydro-2H-pyran with high stereoselectivity. The aryl imines were formed in situ from aromatic amines and arylaldehydes.

  发现脯氨酸三氟甲磺酸酯可有效地催化芳基亚胺和 3,4-二氢-2H-吡喃一锅法合成 2H-吡喃并四氢喹啉，并具有高立体选择性。芳基亚胺由芳香胺和芳醛原位形成。
• Stereoselective synthesis of pyrano[3,2-c]- and furano[3,2-c]quinolines: Gadolinium chloride catalyzed one-pot aza-Diels-Alder reactions
  作者：Yong Yu、Jun Zhou、Zhigang Yao、Fan Xu、Qi Shen

  DOI：10.1002/hc.20612

  日期：——

  A simple and efficient method for the cis-selective synthesis of pyrano- and furano[3,2-c]quinolines via gadolinium chloride catalyzed one-pot aza–Diels–Alder reaction is described. Solvent conditions played a major role in affecting the diastereoselectivity of the products. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:351–354, 2010; Published online in Wiley InterScience (www.interscience.wiley

  描述了一种通过氯化钆催化的单锅氮杂-Diels-Alder反应顺式选择性合成吡喃和呋喃并[3,2-c]喹啉的简单有效方法。溶剂条件在影响产物的非对映选择性方面起主要作用。© 2010 Wiley Periodicals, Inc. 杂原子化学 21:351–354, 2010; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20612
• A Facile and Convenient Three-component Coupling Protocol for the Synthesis of Pyrano and Furoquinolines
  作者：N. Ravindranath、C. Ramesh、M. Ravinder Reddy、Biswanath Das

  DOI：10.1246/cl.2003.222

  日期：2003.3

  Ceric ammonium nitrate (CAN) catalyzes efficiently the coupling of anilines, benzaldehydes and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran to form the corresponding pyrano or furoquinolines in short reaction times and in high yields.

  硝酸铈铵（CAN）可高效催化苯胺、苯甲醛和3,4-二氢-2H-吡喃或2,3-二氢呋喃的偶联反应，在短时间内以高收率生成相应的吡喃或呋喃喹啉。
• Imino Diels–Alder reactions: One-pot synthesis of tetrahydroquinolines
  作者：Vinod T. Kamble、Bhaskar S. Davane、Sanjay A. Chavan、Dnyanoba B. Muley、Sandeep T. Atkore

  DOI：10.1016/j.cclet.2009.11.016

  日期：2010.3

  Abstract An efficient synthesis of tetrahydroquinoline derivatives is reported via three component coupling reactions of aldehydes and anilines with various dienophiles in the presence of a catalytic amount of perchloric acid adsorbed on silica gel (HClO 4 –SiO 2 ) under mild reaction conditions.

  摘要：在温和的反应条件下，在催化量的高氯酸吸附在硅胶上（HClO 4 -SiO 2）的情况下，醛和苯胺与各种亲二烯体的三组分偶联反应可有效合成四氢喹啉衍生物。
• Molecular Iodine-Catalyzed Imino-Diels-Alder Reactions: Efficient One-Pot Synthesis of Pyrano[3,2-<i>c</i>]quinolines
  作者：Min Xia、Yue-dong Lu

  DOI：10.1055/s-2005-872676

  日期：——

  The successful use of molecular iodine as a catalyst in the intermolecular imino-Diels-Alder reaction is described. A one-pot synthesis of pyrano[3,2-c]quinolines was achieved by three-component coupling of aldehydes and anilines with 2,3-dihydropyran catalyzed by iodine. The reactions could be carried out smoothly at room temperature within three to six hours to offer the target products in good yields

  描述了分子碘在分子间亚氨基-Diels-Alder 反应中作为催化剂的成功应用。通过碘催化醛和苯胺与 2,3-二氢吡喃的三组分偶联，实现了吡喃并 [3,2-c] 喹啉的一锅法合成。反应可以在室温下在3-6小时内顺利进行，以良好的收率提供目标产物。我们还研究了溶剂效应、取代基效应和所需的碘量。