3β-tert-butyldimethylsilyloxy-10α-hydroxy-1,5αH,4,6,7βH-aromadendrane | 383126-56-5

• 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-hydroxy-1,5αH,4,6,7βH-aromadendrane
• 英文别名: (1aS,4R,4aR,6S,7S,7aS,7bR)-6-[tert-butyl(dimethyl)silyl]oxy-1,1,4,7-tetramethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-ol
• CAS: 383126-56-5
• 化学式: C₂₁H₄₀O₂Si
• 分子量: 352.633
• InChiKey: GFSRWXNCRGPZBI-YRXFDDPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-tert-butyldimethylsilyloxy-10α-hydroxy-1,5αH,4,6,7βH-aromadendrane 在 吡啶 、 三丁基膦 、 氢氟酸 、 双氧水 、 氧气 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 plagiochiline N
  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：

  甲基锂 、 (1aS,4R,4aR,6S,7S,7aS,7bR)-1,1-Dibromo-6-(tert-butyl-dimethyl-silanyloxy)-4,7-dimethyl-decahydro-cyclopropa[e]azulen-4-ol 、 碘甲烷 在 CuCN 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.17h， 以80%的产率得到3β-tert-butyldimethylsilyloxy-10α-hydroxy-1,5αH,4,6,7βH-aromadendrane
  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.