(2S,3S,4R,4aR,10bS)-ethyl 3,4,4a,5,6,10b-hexahydro-4-hydroxy-3-methyl-2H-benzo[h]chromene-2-carboxylate | 1187319-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3S,4R,4aR,10bS)-ethyl 3,4,4a,5,6,10b-hexahydro-4-hydroxy-3-methyl-2H-benzo[h]chromene-2-carboxylate
• CAS: 1187319-35-2
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: PQXLPYFRJBQPPJ-AHMITGRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (2S,3R,4aS,10bS)-ethyl 3,4,4a,5,6,10b-hexahydro-3-methyl-4-oxo-2H-benzo[h]chromene-2-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以75%的产率得到(2S,3S,4R,4aR,10bS)-ethyl 3,4,4a,5,6,10b-hexahydro-4-hydroxy-3-methyl-2H-benzo[h]chromene-2-carboxylate
  参考文献：
  名称：

  Chiral Phosphoric Acid-Governed Anti-Diastereoselective and Enantioselective Hetero-Diels−Alder Reaction of Glyoxylate

  摘要：

  A highly enantioselective anti-diastereoselective hetero-Diets-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3' positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diets-Alder reactions catalyzed by a chiral Lewis acid.

  DOI：

  10.1021/ja904749x