(4aR,5S,6S,8aR)-5-(((R)-6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl)ethynyl)-5,6,8a-trimethyloctahydronaphthalene-1(2H)-one | 916593-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4aR,5S,6S,8aR)-5-(((R)-6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl)ethynyl)-5,6,8a-trimethyloctahydronaphthalene-1(2H)-one
• 英文别名: (4aR,5S,6S,8aR)-5-[2-[(2R)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethynyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-one
• CAS: 916593-53-8
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: VKQHWEQGCHNICM-LEGFMSBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aR,5S,6S,8aR)-5-(((R)-6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl)ethynyl)-5,6,8a-trimethyloctahydronaphthalene-1(2H)-one 在 potassium tert-butylate 、 氧气 、 rose bengal 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.34h， 生成 5-hydroxy-4-((R)-5-(((1S,2S,4aR,8aS)-1,2,4a-trimethyl-5-methylenedecahydronaphthalen-1-yl)ethynyl)-3,6-dihydro-2H-pyran-2-yl)furan-2(5H)-one
  参考文献：
  名称：

  Conformationally Restricted (+)-Cacospongionolide B Analogues. Influence on Secretory Phospholipase A₂ Inhibition

  摘要：

  A new approach to (+)-cacospongionolide was developed to access conformationally restricted variants of the natural product. The flexible aliphatic region between the decalin and side chain portion of the natural product was replaced with alkenyl and alkynyl linkers to probe the influence of structural rigidity in the inhibition of secretary phospholipase A(2) (sPLA(2)). It was found that when the aliphatic section is replaced with a Z-olefin or an alkyne, sPLA(2) inhibitory activity suffered relative to the natural product; however, an E-olefin-containing analogue led to an enhanced activity. These results suggest that preferred sPLA(2) binding conformation of the natural product is similar to the geometry of the E-olefin-containing analogue.

  DOI：

  10.1021/jo061407a
• 作为产物：
  描述：

  (4a'R,5'S,6'S,8a'R)-5'-(((R)-6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl)ethynyl)-5',6',8a'-trimethyloctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene] 在 水 、 溶剂黄146 作用下， 反应 1.0h， 以88%的产率得到(4aR,5S,6S,8aR)-5-(((R)-6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl)ethynyl)-5,6,8a-trimethyloctahydronaphthalene-1(2H)-one
  参考文献：
  名称：

  Conformationally Restricted (+)-Cacospongionolide B Analogues. Influence on Secretory Phospholipase A₂ Inhibition

  摘要：

  A new approach to (+)-cacospongionolide was developed to access conformationally restricted variants of the natural product. The flexible aliphatic region between the decalin and side chain portion of the natural product was replaced with alkenyl and alkynyl linkers to probe the influence of structural rigidity in the inhibition of secretary phospholipase A(2) (sPLA(2)). It was found that when the aliphatic section is replaced with a Z-olefin or an alkyne, sPLA(2) inhibitory activity suffered relative to the natural product; however, an E-olefin-containing analogue led to an enhanced activity. These results suggest that preferred sPLA(2) binding conformation of the natural product is similar to the geometry of the E-olefin-containing analogue.

  DOI：

  10.1021/jo061407a