3β-tert-butyldimethylsilyloxy-10α-trimethoxysilyloxy-1,5αH,4,6βH-guai-7(11)-en-6,12-olide | 383126-51-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-tert-butyldimethylsilyloxy-10α-trimethoxysilyloxy-1,5αH,4,6βH-guai-7(11)-en-6,12-olide
• 英文别名: (6R,6aR,8S,9S,9aS,9bR)-8-[tert-butyl(dimethyl)silyl]oxy-3,6,9-trimethyl-6-trimethylsilyloxy-4,5,6a,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• CAS: 383126-51-0
• 化学式: C₂₄H₄₄O₄Si₂
• 分子量: 452.782
• InChiKey: MRKVRLADUANCTI-IAKILTLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  3β-tert-butyldimethylsilyloxy-10α-trimethoxysilyloxy-1,5αH,4,6βH-guai-7(11)-en-6,12-olide 在 氧气 、 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以94%的产率得到[(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
• 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 、 sodium hexamethyldisilazane 、 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 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.41h， 生成 3β-tert-butyldimethylsilyloxy-10α-trimethoxysilyloxy-1,5αH,4,6βH-guai-7(11)-en-6,12-olide
  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.