(S)-3-(Fluoro-dimethyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione | 600155-06-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: (S)-3-(Fluoro-dimethyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione
• 英文别名: (3S)-3-[fluoro(dimethyl)silyl]-8-hydroxy-3-methyl-2,4-dihydro-1H-benzo[a]anthracene-7,12-dione
• CAS: 600155-06-4
• 化学式: C₂₁H₂₁FO₃Si
• 分子量: 368.48
• InChiKey: CXPKXWKRTVORBV-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(Fluoro-dimethyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione 在 potassium fluoride 、 双氧水 、 碳酸氢钠 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (3S)-3-hydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydro-benz[a]anthracene-7,12-dione
  参考文献：
  名称：

  Remote stereochemical control in asymmetric Diels–Alder reactions: synthesis of the angucycline antibiotics, (−)-tetrangomycin and MM 47755

  摘要：

  The first asymmetric syntheses of the angucycline antibiotics, (-)-tetrangomycin and MM 47755, are achieved via a short efficient sequence starting from the chiral Lewis acid promoted Diels-Alder reaction of 5-hydroxy-1,4-naphthoquinone and (+/-)-(E)-5-dimethylphenylsilyl-5-methyl-1-(2'-trimethylsiloxyvinyl)cyclohexene 7 where an effective kinetic resolution of the latter, controlled by its remote stereocentre, is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01228-0
• 作为产物：
  描述：

  5-羟基对萘醌 在 硼烷四氢呋喃络合物 、 air 、 三氟化硼乙醚 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 (S)-3,3'-diphenyl-2,2'-dihydroxy-1,1'-binaphthyl 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-3-(Fluoro-dimethyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-dione
  参考文献：
  名称：

  Remote stereochemical control in asymmetric Diels–Alder reactions: synthesis of the angucycline antibiotics, (−)-tetrangomycin and MM 47755

  摘要：

  The first asymmetric syntheses of the angucycline antibiotics, (-)-tetrangomycin and MM 47755, are achieved via a short efficient sequence starting from the chiral Lewis acid promoted Diels-Alder reaction of 5-hydroxy-1,4-naphthoquinone and (+/-)-(E)-5-dimethylphenylsilyl-5-methyl-1-(2'-trimethylsiloxyvinyl)cyclohexene 7 where an effective kinetic resolution of the latter, controlled by its remote stereocentre, is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01228-0

文献信息

• Remote stereochemical control in asymmetric Diels–Alder reactions: synthesis of the angucycline antibiotics, (−)-tetrangomycin and MM 47755
  作者：John S. Landells、David S. Larsen、Jim Simpson

  DOI：10.1016/s0040-4039(03)01228-0

  日期：2003.7

  The first asymmetric syntheses of the angucycline antibiotics, (-)-tetrangomycin and MM 47755, are achieved via a short efficient sequence starting from the chiral Lewis acid promoted Diels-Alder reaction of 5-hydroxy-1,4-naphthoquinone and (+/-)-(E)-5-dimethylphenylsilyl-5-methyl-1-(2'-trimethylsiloxyvinyl)cyclohexene 7 where an effective kinetic resolution of the latter, controlled by its remote stereocentre, is described. (C) 2003 Elsevier Science Ltd. All rights reserved.