5-chloro-7,10-dihydro-7,10-epoxy-benzo[h]quinoline | 1274655-71-8

• 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: 5-chloro-7,10-dihydro-7,10-epoxy-benzo[h]quinoline
• 英文别名: 9-Chloro-15-oxa-4-azatetracyclo[10.2.1.02,11.03,8]pentadeca-2,4,6,8,10,13-hexaene
• CAS: 1274655-71-8
• 化学式: C₁₃H₈ClNO
• 分子量: 229.666
• InChiKey: XRGLISIZXNPRKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-7,10-dihydro-7,10-epoxy-benzo[h]quinoline 、 二异丙胺 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33%的产率得到9,10-dihydro-9-(diisopropyl)-benzo[h]quinolin-10-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
• 作为产物：
  描述：

  氯碘羟喹 在 吡啶 、 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 5-chloro-7,10-dihydro-7,10-epoxy-benzo[h]quinoline
  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