2-[3-[(1R)-1-(furan-3-yl)but-3-enoxy]prop-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 916593-48-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 2-[3-[(1R)-1-(furan-3-yl)but-3-enoxy]prop-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 916593-48-1
• 化学式: C₁₇H₂₅BO₄
• 分子量: 304.194
• InChiKey: RCYIZFMNKCJAJW-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[3-[(1R)-1-(furan-3-yl)but-3-enoxy]prop-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 苯 为溶剂， 生成 2-(6-(furan-3-yl)-5,6-dihydro-2H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  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：

  (R)-1-(furan-3-yl)but-3-en-1-ol 在 15-冠醚-5 、 叔丁基锂 、 sodium hydride 作用下， 以 乙醚 、 正戊烷 、 苯 为溶剂， 反应 9.0h， 生成 2-[3-[(1R)-1-(furan-3-yl)but-3-enoxy]prop-1-en-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  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

文献信息

• Conformationally Restricted (+)-Cacospongionolide B Analogues. Influence on Secretory Phospholipase A₂ Inhibition
  作者：Ryan P. Murelli、Atwood K. Cheung、Marc L. Snapper

  DOI：10.1021/jo061407a

  日期：2007.3.1

  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.