(E)-ethyl 13-((tetrahydro-2H-pyran-2-yl)oxy)tridec-2-enoate | 76063-03-1

• 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: (E)-ethyl 13-((tetrahydro-2H-pyran-2-yl)oxy)tridec-2-enoate
• 英文别名: ethyl 13-tetrahydro-2H-2-pyranyloxy-(E)-2-tridecanoate；ethyl 13-tetrahydropyranyloxy-2(E)-tridecenoate；ethyl (E)-13-(oxan-2-yloxy)tridec-2-enoate
• CAS: 76063-03-1
• 化学式: C₂₀H₃₆O₄
• 分子量: 340.503
• InChiKey: YLIQVRGBOVPNFR-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 13-((tetrahydro-2H-pyran-2-yl)oxy)tridec-2-enoate 在 盐酸 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 22.5h， 生成 (E)-11-十四碳烯-1-醇
  参考文献：
  名称：

  Vig, O. P.; Sharma, M. L.; Verma, N. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 7, p. 581 - 582

  摘要：

  DOI：
• 作为产物：
  描述：

  10-溴-1-癸醇 在 18-冠醚-6 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 76.0h， 生成 (E)-ethyl 13-((tetrahydro-2H-pyran-2-yl)oxy)tridec-2-enoate
  参考文献：
  名称：

  Total synthesis of motualevic acids A–F, (E) and (Z)-antazirines

  摘要：

  Total synthesis of motualevic acids A-F and (E) & (Z) geometrical isomers of antazirines has been achieved from a commercially available starting material, 1,10-decanediol. The synthesis of motualevic acid E served as a common key intermediate for the synthesis of most of these natural products. The key steps involved in this synthesis were Wittig olefination, Corey-Fuchs reaction, Neber reaction, amide coupling. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.092

文献信息

• An improved and novel approach to macrolactonisation using di-tert-butyl dicarbonate
  作者：M. Nagarajan、V.Satish Kumar、B.Venkateswara Rao

  DOI：10.1016/s0040-4020(99)00718-8

  日期：1999.10

  A new, facile, mild and simple method for the synthesis of macrolides was achieved from omega- hydroxy acids using di-tert-butyl dicarbonate ( Boc(2)O), a cheap and commercially available reagent. A wide range of substrates were tested and give good yield of lactones. The effect of various simple bases on the yield of the macrolactonisation reaction was also studied. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Total synthesis of motualevic acids A–E
  作者：Gangarajula Sudhakar、Vilas D. Kadam、Vaddu V.N. Reddy

  DOI：10.1016/j.tetlet.2009.12.113

  日期：2010.2

  The first total synthesis of motualevic acids A-E, isolated from Siliquariaspongia sp., starting from commercially available 1,10-decanediol, is described. The key steps in the synthetic sequence involve stereoselective olefination, Corey-Fuchs reaction, and amide coupling. (C) 2010 Published by Elsevier Ltd.