(+)-2-[1-(furan-3-yl)-but-3-enyl]oxy-N-methoxy-N-methyl-acetamide | 474055-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (+)-2-[1-(furan-3-yl)-but-3-enyl]oxy-N-methoxy-N-methyl-acetamide
• 英文别名: 2-[(1R)-1-(furan-3-yl)but-3-enoxy]-N-methoxy-N-methylacetamide
• CAS: 474055-47-5
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: RKUDMGYHVLERCQ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-2-[1-(furan-3-yl)-but-3-enyl]oxy-N-methoxy-N-methyl-acetamide 在 Grubbs catalyst first generation 氨 、 lithium 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成 (4aR,8R,8aR)-8-[2-[(2S)-2-(furan-3-yl)-3,6-dihydro-2H-pyran-5-yl]ethyl]-4a,8-dimethyl-7-methylidenespiro[1,2,3,5,6,8a-hexahydronaphthalene-4,2'-1,3-dioxolane]
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e
• 作为产物：
  描述：

  (R)-1-(furan-3-yl)but-3-en-1-ol 在 4-二甲氨基吡啶 、 lithium hydroxide 、 TEA 、 sodium hydride 、 达卡巴嗪 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 15.5h， 生成 (+)-2-[1-(furan-3-yl)-but-3-enyl]oxy-N-methoxy-N-methyl-acetamide
  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.
• Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition
  作者：Atwood K. Cheung、Ryan Murelli、Marc L. Snapper

  DOI：10.1021/jo049285e

  日期：2004.8.1

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.