(2R,3R,4aS,5R,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-2,3,4a,5,8,8a-hexahydro-[1,4]naphthoquinone | 852065-05-5

• 英文名称: (2R,3R,4aS,5R,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-2,3,4a,5,8,8a-hexahydro-[1,4]naphthoquinone
• CAS: 852065-05-5
• 化学式: C₁₆H₂₆O₅Si
• 分子量: 326.465
• InChiKey: JIOCOCQPUZWDJC-TVMMDAIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4aS,5R,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-2,3,4a,5,8,8a-hexahydro-[1,4]naphthoquinone 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到(2R,3R,4aS,5R,8aS)-2,3,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2,3,4a,5,8,8a-hexahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  Studies into the Stereoselectivity of Tartrate-Derived Dienophiles

  摘要：

  Diels-Alder reactions of 1-(tert-butyidimethylsiloxy)-1,3-butadiene (3) with three C2 symmetric dienophiles derived from tartaric acid have been examined. Complementary diastereoselectivity is observed depending on the nature of the 1,2-diol protecting group incorporated in these dienophiles.

  DOI：

  10.1021/ol050105c
• 作为产物：
  描述：

  (3aR,4aS,5R,8aS,9aR)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4a,5,8,8a,9a-hexahydro-naphtho[2,3-d][1,3]dioxole-4,9-dione 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以74%的产率得到(2R,3R,4aS,5R,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-2,3,4a,5,8,8a-hexahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  Studies into the Stereoselectivity of Tartrate-Derived Dienophiles

  摘要：

  Diels-Alder reactions of 1-(tert-butyidimethylsiloxy)-1,3-butadiene (3) with three C2 symmetric dienophiles derived from tartaric acid have been examined. Complementary diastereoselectivity is observed depending on the nature of the 1,2-diol protecting group incorporated in these dienophiles.

  DOI：

  10.1021/ol050105c