[(2S,3S,3aS,4R,8R,8aR)-2-[tert-butyl(dimethyl)silyl]oxy-3,8-dimethyl-5-oxo-8-trimethylsilyloxy-1,2,3,3a,4,6,7,8a-octahydroazulen-4-yl] 2-oxopropanoate | 383126-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,3aS,4R,8R,8aR)-2-[tert-butyl(dimethyl)silyl]oxy-3,8-dimethyl-5-oxo-8-trimethylsilyloxy-1,2,3,3a,4,6,7,8a-octahydroazulen-4-yl] 2-oxopropanoate
• CAS: 383126-52-1
• 化学式: C₂₄H₄₄O₆Si₂
• 分子量: 484.781
• InChiKey: VCLIKTYJKBEFDZ-UFLCQEFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3S,3aS,4R,8R,8aR)-2-[tert-butyl(dimethyl)silyl]oxy-3,8-dimethyl-5-oxo-8-trimethylsilyloxy-1,2,3,3a,4,6,7,8a-octahydroazulen-4-yl] 2-oxopropanoate 在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 以25%的产率得到(2S,3S,3aS,4R,5R,8R,8aR)-2-(tert-Butyl-dimethyl-silanyloxy)-3,8-dimethyl-8-trimethylsilanyloxy-decahydro-azulene-4,5-diol
  参考文献：
  名称：

  Synthesis of Plagiochiline N from Santonin

  摘要：

  This article reports the transformation of O-acetylisophotosantonin, obtained by photochemical rearrangement of santonin, into plagiochiline N, an ent-2,3-secoaromadendrane isolated from Plagiochila ovalifolia. The synthesis was carried out in a sequence involving as the key steps (a) the substitution of the lactone moiety by a gem-dimethylcyclopropane ring through a synthetic intermediate having a C-6-C-7 double bond and (b) the ozonolysis of the C-2-C-3 bond followed by cyclization to the dihydropyran ring characteristic of plagiochiline N. Spectroscopic data of the synthetic product fully coincided with the reported data for the natural product.

  DOI：

  10.1021/jo010567d
• 作为产物：
  描述：

  O-acetylisophotosantonic lactone 在 咪唑 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 sodium hydrogen telluride 、 氧气 、 sodium hexamethyldisilazane 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.41h， 生成 [(2S,3S,3aS,4R,8R,8aR)-2-[tert-butyl(dimethyl)silyl]oxy-3,8-dimethyl-5-oxo-8-trimethylsilyloxy-1,2,3,3a,4,6,7,8a-octahydroazulen-4-yl] 2-oxopropanoate
  参考文献：
  名称：

  Synthesis of Plagiochiline N from Santonin

  摘要：

  This article reports the transformation of O-acetylisophotosantonin, obtained by photochemical rearrangement of santonin, into plagiochiline N, an ent-2,3-secoaromadendrane isolated from Plagiochila ovalifolia. The synthesis was carried out in a sequence involving as the key steps (a) the substitution of the lactone moiety by a gem-dimethylcyclopropane ring through a synthetic intermediate having a C-6-C-7 double bond and (b) the ozonolysis of the C-2-C-3 bond followed by cyclization to the dihydropyran ring characteristic of plagiochiline N. Spectroscopic data of the synthetic product fully coincided with the reported data for the natural product.

  DOI：

  10.1021/jo010567d

文献信息

• Synthesis of Plagiochiline N from Santonin
  作者：Gonzalo Blay、Luz Cardona、Begoña García、Luisa Lahoz、José R. Pedro

  DOI：10.1021/jo010567d

  日期：2001.11.1

  This article reports the transformation of O-acetylisophotosantonin, obtained by photochemical rearrangement of santonin, into plagiochiline N, an ent-2,3-secoaromadendrane isolated from Plagiochila ovalifolia. The synthesis was carried out in a sequence involving as the key steps (a) the substitution of the lactone moiety by a gem-dimethylcyclopropane ring through a synthetic intermediate having a C-6-C-7 double bond and (b) the ozonolysis of the C-2-C-3 bond followed by cyclization to the dihydropyran ring characteristic of plagiochiline N. Spectroscopic data of the synthetic product fully coincided with the reported data for the natural product.