(3aR,10bR)-3,3a-dihydro-[1,3]dioxolo[4',5':6,7]naphtho[2,1-d]oxazol-2(10bH)-one | 1422462-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3aR,10bR)-3,3a-dihydro-[1,3]dioxolo[4',5':6,7]naphtho[2,1-d]oxazol-2(10bH)-one
• 英文别名: (3aR,10bR)-3a,10b-dihydro-3H-[1,3]benzodioxolo[5,6-g][1,3]benzoxazol-2-one
• CAS: 1422462-40-5
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: DIIMOXOHZVSGAF-LDYMZIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium isocyanate 、 5,8-dihydro-5,8-epoxynaphtho[2,3-d]-1,3-dioxole 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52%的产率得到(3aR,10bR)-3,3a-dihydro-[1,3]dioxolo[4',5':6,7]naphtho[2,1-d]oxazol-2(10bH)-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).