2-dodecyl-4-(2-oxopropyl)-2H-furan-5-one | 1384097-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-dodecyl-4-(2-oxopropyl)-2H-furan-5-one
• CAS: 1384097-98-6
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: MDYNACLNBIKSIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-iodotridecane 在 咪唑 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 正丁基锂 、 叔丁基锂 、 氧气 、 亚甲兰 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 为溶剂， 反应 38.58h， 生成 2-dodecyl-4-(2-oxopropyl)-2H-furan-5-one
  参考文献：
  名称：

  First Total Synthesis of Paracaseolide A

  摘要：

  The first total synthesis of the paracaseolide A, a very unusual tetraquinane oxa-cage bislactone recently isolated from the mangrove Sonneratia paracaseolaris, has been achieved. The final step and culmination of the eight-step synthetic sequence is a [4 + 2] dimerization of a 4-hydroxybutenolide, generated by singlet oxygen-mediated oxidation of a furan precursor.

  DOI：

  10.1021/ol301481t

文献信息

• Total synthesis of novel bioactive natural product paracaseolide A and analogues: computational evaluation of a ‘proposed’ biomimetic Diels–Alder reaction
  作者：Laxmaiah Vasamsetty、Debashis Sahu、Bishwajit Ganguly、Faiz Ahmed Khan、Goverdhan Mehta

  DOI：10.1016/j.tet.2014.09.072

  日期：2014.11

  A short and generally applicable synthesis of bioactive tetracyclic natural product paracaseolide A has been accomplished employing a ‘proposed’ biomimetic Diels–Alder reaction as the key strategic step. The Diels–Alder precursors for this purpose were readily assembled through a versatile Suzuki coupling on preformed α-halo butenolides. The mechanistic aspects of the ‘putative’ biomimetic Diels–Alder

  使用拟议的仿生狄尔斯-阿尔德反应作为关键的战略性步骤，已完成了对生物活性四环天然产物对酪蛋白内酯A的短暂合成且普遍适用。为此，Diels–Alder前体可通过通用的Suzuki偶联剂容易地组装在预先形成的α-卤代丁烯内酯上。已使用计算方法探究了“公认的”仿生Diels-Alder反应的机理，这表明这种[4 + 2]-环加成反应是通过逐步过程进行的，并且产物的分布是受热力学控制的。
• Total synthesis of (±)-paracaseolide A and initial attempts at a Lewis acid mediated dimerization of its putative biosynthetic precursor
  作者：David S. Giera、Christian B. W. Stark

  DOI：10.1039/c3ra44590a

  日期：——

  A short (5 steps) and highly efficient (25% overall yield) synthesis of paracaseolide A is described. Crucial steps are an α-iodination of a butenolide, a Suzuki coupling and a thermal Diels–Alder reaction. In attempts at Lewis acid catalyzed [4 + 2]-cycloadditions a set of novel dimerization products of the proposed biosynthetic paracaseolide A precursor were produced.

  描述了对干酪素A的短（5步）和高效（总收率25％）合成。关键步骤是丁烯内酯的α-碘化，Suzuki偶联和Diels-Alder热反应。在路易斯酸催化的[4 + 2]-环加成反应中，制备了一组新的拟合成的生物合成对乙酰酪酚A前体的二聚产物。
• Total synthesis of a novel oxa-bowl natural product paracaseolide A via a ‘putative’ biomimetic pathway
  作者：Laxmaiah Vasamsetty、Faiz Ahmed Khan、Goverdhan Mehta

  DOI：10.1016/j.tetlet.2013.04.097

  日期：2013.7

  A total synthesis of bioactive tetracyclic natural product paracaseolide A, embodying an architecturally unusual oxa-bowl framework, has been accomplished from commercially available 5-methyl-2-furfural. The key step involving a thermal [4+2]-dimerization of an appropriately crafted 5-methyl-3-alkenylbutenolide is shown to proceed in a stepwise manner. (c) 2013 Elsevier Ltd. All rights reserved.