(3aR,9bR)-6,9-dimethoxy-3,3a-dihydronaphtho[2,1-d]oxazol-2(9bH)-one | 1422462-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3aR,9bR)-6,9-dimethoxy-3,3a-dihydronaphtho[2,1-d]oxazol-2(9bH)-one
• 英文别名: (3aR,9bR)-6,9-dimethoxy-3a,9b-dihydro-3H-benzo[g][1,3]benzoxazol-2-one
• CAS: 1422462-46-1
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: AGRVYOWHCBPXEY-PELKAZGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,9bR)-6,9-dimethoxy-3,3a-dihydronaphtho[2,1-d]oxazol-2(9bH)-one 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.17h， 以52%的产率得到(3aR,9bR)-6,9-dimethoxy-3-tosyl-3,3a-dihydronaphtho[2,1-d]oxazol-2(9bH)-one
  参考文献：
  名称：

  Expedient Synthesis of Chiral Oxazolidinone Scaffolds via Rhodium-Catalyzed Asymmetric Ring-Opening with Sodium Cyanate

  摘要：

  A method for synthesizing chiral oxazolidinone scaffolds from readily available oxabicyclic alkenes is described. The reaction utilizes a domino sequence of Rh(I)-catalyzed asymmetric ring-opening (ARO) with sodium cyanate as a novel nucleophile followed by intramolecular cyclization to generate oxazolidinone products in excellent enantioselectivities (trans stereochemistry).

  DOI：

  10.1021/ol4000668
• 作为产物：
  描述：

  1,4-dihydro-5,8-dimethoxy-1,4-epoxynaphthalene 、 sodium isocyanate 在 bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine 、 三乙胺盐酸盐 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 以73%的产率得到(3aR,9bR)-6,9-dimethoxy-3,3a-dihydronaphtho[2,1-d]oxazol-2(9bH)-one
  参考文献：
  名称：

  Expedient Synthesis of Chiral Oxazolidinone Scaffolds via Rhodium-Catalyzed Asymmetric Ring-Opening with Sodium Cyanate

  摘要：

  A method for synthesizing chiral oxazolidinone scaffolds from readily available oxabicyclic alkenes is described. The reaction utilizes a domino sequence of Rh(I)-catalyzed asymmetric ring-opening (ARO) with sodium cyanate as a novel nucleophile followed by intramolecular cyclization to generate oxazolidinone products in excellent enantioselectivities (trans stereochemistry).

  DOI：

  10.1021/ol4000668

文献信息

• Expedient Synthesis of Chiral Oxazolidinone Scaffolds via Rhodium-Catalyzed Asymmetric Ring-Opening with Sodium Cyanate
  作者：Gavin Chit Tsui、Nina M. Ninnemann、Akihito Hosotani、Mark Lautens

  DOI：10.1021/ol4000668

  日期：2013.3.1

  A method for synthesizing chiral oxazolidinone scaffolds from readily available oxabicyclic alkenes is described. The reaction utilizes a domino sequence of Rh(I)-catalyzed asymmetric ring-opening (ARO) with sodium cyanate as a novel nucleophile followed by intramolecular cyclization to generate oxazolidinone products in excellent enantioselectivities (trans stereochemistry).