(2E)-ethyl 3-((5E)-1-oxodec-5-en-4-yloxy)prop-2-enoate | 1292793-73-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E)-ethyl 3-((5E)-1-oxodec-5-en-4-yloxy)prop-2-enoate
• CAS: 1292793-73-7
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: PDPFYLGZGRNKIF-PTSVWTKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  19.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E)-ethyl 3-((5E)-1-oxodec-5-en-4-yloxy)prop-2-enoate 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 生成 ethyl 2-((2RS,3SR,6SR,E)-6-hexenyl-3-hydroxytetrahydro-2H-pyran-2-yl)acetate 、 ethyl 2-((2RS,3SR,6RS,E)-6-hexenyl-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Formal total synthesis of aspergillide A

  摘要：

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.016
• 作为产物：
  描述：

  ethyl (E)-3-(((E)-1-(1,3-dithian-2-yl)non-4-en-3-yl)oxy)acrylate 在 碳酸氢钠 、 碘甲烷 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以64 mg的产率得到(2E)-ethyl 3-((5E)-1-oxodec-5-en-4-yloxy)prop-2-enoate
  参考文献：
  名称：

  Formal total synthesis of aspergillide A

  摘要：

  The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C-4-C-14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into beta-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.016