(3R,4S,4aR,11bS)-3,4-dihydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(11bH)-one | 1161437-21-3

• 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: (3R,4S,4aR,11bS)-3,4-dihydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(11bH)-one
• 英文别名: (3R,4S,4aR,11bS)-3,4-dihydroxy-4,4a,5,11b-tetrahydro-3H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• CAS: 1161437-21-3
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: NQKDIWZRDUGNHJ-RFMQNAQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-bromo-N-((1R,5R,6S)-5,6-dihydroxycyclohex-2-enyl)benzo[d][1,3]dioxole-5-carboxamide 在 2,2,6,6-四甲基哌啶 、 palladium diacetate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以39%的产率得到(3R,4S,4aR,11bS)-3,4-dihydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(11bH)-one
  参考文献：
  名称：

  Desymmetrization of Hydrazinocyclohexadienes: A New Approach for the Synthesis of Polyhydroxylated Aminocyclohexanes

  摘要：

  Hydrazinocyclohexadienes, easily prepared by an ene-reaction between commercially available azodicarboxylate reagents and cyclohexadiene, are interesting substrates for desymmetrization reactions. Under Sharpless asymmetric dihydroxylation conditions, they can lead efficiently to several chiral building blocks as well as advanced precursors of biologically active compounds.

  DOI：

  10.1021/ol900779v