6-(3,4-dihydro-1(2H)-quinolinyl)-5,6-dihydroisoquinolin-5-ol | 1274655-37-6

• 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: 6-(3,4-dihydro-1(2H)-quinolinyl)-5,6-dihydroisoquinolin-5-ol
• 英文别名: (5R,6R)-6-(3,4-dihydro-2H-quinolin-1-yl)-5,6-dihydroisoquinolin-5-ol
• CAS: 1274655-37-6
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: IAJODNMCPVCXNC-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,8-epoxy-5,8-dihydroisoquinoline 、 1,2,3,4-四氢喹啉 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到6-(3,4-dihydro-1(2H)-quinolinyl)-5,6-dihydroisoquinolin-5-ol
  参考文献：
  名称：

  Rh(I)-Catalyzed Ring-Opening of Hetaryne−Furan Diels−Alder Adducts: Rapid Access to Stereochemically Defined Heterocyclic Scaffolds

  摘要：

  Probing the nucleophilic ring-opening of various bicyclic [2.2.1] hetaryne-furan Diels-Alder adducts revealed that efficient reactivity could be observed with heteroatom nucleophiles by using a cationic Rh(I) complex in combination with a chiral Josiphos-type phosphine ligand. Remarkably, this catalyst system was not impeeded by the incorporation of a heteroatom into the substrate. Racemic materials afforded separable mixtures of enantioenriched regioisomers, indicating that strong reagent control is operative.

  DOI：

  10.1021/ol200057j

文献信息

• Rh(I)-Catalyzed Ring-Opening of Hetaryne−Furan Diels−Alder Adducts: Rapid Access to Stereochemically Defined Heterocyclic Scaffolds
  作者：Trung D. Nguyen、Robert Webster、Mark Lautens

  DOI：10.1021/ol200057j

  日期：2011.3.18

  Probing the nucleophilic ring-opening of various bicyclic [2.2.1] hetaryne-furan Diels-Alder adducts revealed that efficient reactivity could be observed with heteroatom nucleophiles by using a cationic Rh(I) complex in combination with a chiral Josiphos-type phosphine ligand. Remarkably, this catalyst system was not impeeded by the incorporation of a heteroatom into the substrate. Racemic materials afforded separable mixtures of enantioenriched regioisomers, indicating that strong reagent control is operative.