(+/-)-spongia-13α,15-diol | 100349-44-8

• 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: (+/-)-spongia-13α,15-diol
• 英文别名: (1S,2R,4aS,4bR,8aR,10aS)-1-(hydroxymethyl)-2,4b,8,8,10a-pentamethyl-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ol
• CAS: 100349-44-8
• 化学式: C₂₀H₃₆O₂
• 分子量: 308.505
• InChiKey: HSSHRMRFCHARFX-HEMOKCEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-spongia-13α,15-diol 在 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 45.0h， 生成
  参考文献：
  名称：

  Strongylophorine-26, an Inhibitor of Cancer Cell Invasion:  SAR Revealed by Synthesis of Analogues

  摘要：

  The absolute configuration of strongylophorine-26 (1) was determined to be 4S, 5R, 8R, 9S, 10S, 13S, 14S by single-crystal X-ray diffraction analysis of the derivative 7 prepared from the co-occurring metabolite strongylophorine-8 (4) and chemical interconversion to the bislactone 8. Synthetic analogues (+)- and (-)-3 have been prepared in order to explore the structure-activity relationship for the anti-invasion pharmacophore of stronglylophorine-26. These studies revealed the unanticipated importance of the A ring lactone moiety for the anti-invasion activity of 1.

  DOI：

  10.1021/np060481l
• 作为产物：
  描述：

  geranylgeranyl acetate 生成 (+/-)-spongia-13α,15-diol
  参考文献：
  名称：

  Chemical simulation of polycyclic diterpenoid biosynthesis using mercury(II) triflate/N,N-dimethylaniline complex: mechanistic aspects of a biomimetic olefin cyclization

  摘要：

  DOI：

  10.1021/jo00356a008

文献信息

• The C-13 configuration of the bromine-containing diterpene isoaplysin-20. Synthesis of debromoisoaplysin-20 and C-13 epimer
  作者：Paulo M. Imamura、Edmundo A. Ruveda

  DOI：10.1021/jo01291a028

  日期：1980.2
• Chemical simulation of polycyclic diterpenoid biosynthesis using mercury(II) triflate/N,N-dimethylaniline complex: mechanistic aspects of a biomimetic olefin cyclization
  作者：Mugio Nishizawa、Hideyuki Takenaka、Yuji Hayashi

  DOI：10.1021/jo00356a008

  日期：1986.3
• Strongylophorine-26, an Inhibitor of Cancer Cell Invasion:  SAR Revealed by Synthesis of Analogues
  作者：Kaoru Warabi、Brian O. Patrick、Pamela Austin、Calvin D. Roskelley、Michel Roberge、Raymond J. Andersen

  DOI：10.1021/np060481l

  日期：2007.5.25

  The absolute configuration of strongylophorine-26 (1) was determined to be 4S, 5R, 8R, 9S, 10S, 13S, 14S by single-crystal X-ray diffraction analysis of the derivative 7 prepared from the co-occurring metabolite strongylophorine-8 (4) and chemical interconversion to the bislactone 8. Synthetic analogues (+)- and (-)-3 have been prepared in order to explore the structure-activity relationship for the anti-invasion pharmacophore of stronglylophorine-26. These studies revealed the unanticipated importance of the A ring lactone moiety for the anti-invasion activity of 1.