(-)-2-(furan-3-yl)-5-[2-(1,2,4a-trimethyl-5-methylene-decahydronaphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran | 474055-50-0

• 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: (-)-2-(furan-3-yl)-5-[2-(1,2,4a-trimethyl-5-methylene-decahydronaphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran
• 英文别名: (2S)-5-[2-[(1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-2-(furan-3-yl)-3,6-dihydro-2H-pyran
• CAS: 474055-50-0
• 化学式: C₂₅H₃₆O₂
• 分子量: 368.56
• InChiKey: JWRONCHLASWCIS-BHEUDDMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-2-(furan-3-yl)-5-[2-(1,2,4a-trimethyl-5-methylene-decahydronaphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran 在 氧气 、 rose bengal 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-cacospongionolide B
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B:  New Insight into Structural Requirements for Phospholipase A₂ Inhibition

  摘要：

  The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/ja026899x
• 作为产物：
  描述：

  (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium 、 氢气 、 lithium 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氨 、 二甲基亚砜 为溶剂， -78.0~75.0 ℃ 、303.99 kPa 条件下， 生成 (-)-2-(furan-3-yl)-5-[2-(1,2,4a-trimethyl-5-methylene-decahydronaphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B:  New Insight into Structural Requirements for Phospholipase A₂ Inhibition

  摘要：

  The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/ja026899x

文献信息

• Total Syntheses of (+)- and (−)-Cacospongionolide B:  New Insight into Structural Requirements for Phospholipase A₂ Inhibition
  作者：Atwood K. Cheung、Marc L. Snapper

  DOI：10.1021/ja026899x

  日期：2002.10.1

  The first total synthesis of the antiinflammatory marine sponge metabolite (+)-cacospongionolide B has been accomplished in 12 linear steps. The pivotal transformations include a three-step sequence coupling the two main regions of the natural product as well as generating the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that cacospongionolide B has an enantiospecific interaction with the enzyme that is independent of the gamma-hydroxybutenolide moiety.