3β-tert-butyldimethylsilyloxy-11β-hydroxy-10α-trimethoxysilyloxy-1,5,7αH,4,6,11βH-guaian-6,12-olide | 383126-50-9

• 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-11β-hydroxy-10α-trimethoxysilyloxy-1,5,7αH,4,6,11βH-guaian-6,12-olide
• 英文别名: (3R,3aR,6R,6aR,8S,9S,9aS,9bR)-8-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-3,6,9-trimethyl-6-trimethylsilyloxy-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• CAS: 383126-50-9
• 化学式: C₂₄H₄₆O₅Si₂
• 分子量: 470.797
• InChiKey: OSNSVTCDDDBHSY-RKVFQHHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-tert-butyldimethylsilyloxy-11β-hydroxy-10α-trimethoxysilyloxy-1,5,7αH,4,6,11βH-guaian-6,12-olide 在 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 、 甲苯 为溶剂， 反应 2.83h， 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
• 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 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.58h， 生成 3β-tert-butyldimethylsilyloxy-11β-hydroxy-10α-trimethoxysilyloxy-1,5,7αH,4,6,11βH-guaian-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.