10α-hydroxy-1,5αH,4,6,7βH-2-aromadendrene | 383126-59-8

• 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: 10α-hydroxy-1,5αH,4,6,7βH-2-aromadendrene
• 英文别名: (1aS,4R,4aR,7R,7aR,7bR)-1,1,4,7-tetramethyl-2,3,4a,7,7a,7b-hexahydro-1aH-cyclopropa[e]azulen-4-ol
• CAS: 383126-59-8
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: OZXPXMCNURABDU-ITTXBHIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10α-hydroxy-1,5αH,4,6,7βH-2-aromadendrene 在 氧气 、 臭氧 、 二甲基硫 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 37.0h， 以27%的产率得到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：

  3β-tert-butyldimethylsilyloxy-10α-hydroxy-1,5αH,4,6,7βH-aromadendrane 在 吡啶 、 三丁基膦 、 氢氟酸 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 10α-hydroxy-1,5αH,4,6,7βH-2-aromadendrene
  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.