(2S,3R,10bR)-ethyl 4-t-buthyldimethylsiloxy-3,5,6,10b-tetrahydro-3-methyl-2H-benzo[h]chromene-carboxylate | 1187319-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3R,10bR)-ethyl 4-t-buthyldimethylsiloxy-3,5,6,10b-tetrahydro-3-methyl-2H-benzo[h]chromene-carboxylate
• 英文别名: ethyl (2S,3R,10bR)-4-[tert-butyl(dimethyl)silyl]oxy-3-methyl-3,5,6,10b-tetrahydro-2H-benzo[h]chromene-2-carboxylate
• CAS: 1187319-24-9
• 化学式: C₂₃H₃₄O₄Si
• 分子量: 402.606
• InChiKey: PXQBGINCEJILRQ-ONGXBYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,10bR)-ethyl 4-t-buthyldimethylsiloxy-3,5,6,10b-tetrahydro-3-methyl-2H-benzo[h]chromene-carboxylate 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以74%的产率得到(2S,3R,4aS,10bS)-ethyl 3,4,4a,5,6,10b-hexahydro-3-methyl-4-oxo-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
• 作为产物：
  描述：

  乙醛酸乙酯 、 (1-(1,2-dihydronaphthalen-3-yl)prop-1-enyloxy)(t-butyl)dimethylsilane 在 (R_a)-4-hydroxy-2,6-diphenyldinaphtho[1,3,2]dioxaphosphepine 4-oxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (2S,3R,10bR)-ethyl 4-t-buthyldimethylsiloxy-3,5,6,10b-tetrahydro-3-methyl-2H-benzo[h]chromene-carboxylate 、 (2S,3S,10bS)-ethyl 4-t-buthyldimethylsiloxy-3,5,6,10b-tetrahydro-3-methyl-2H-benzo[h]chromene-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