ethyl (2E,4E)-6-[(tetrahydro-2H-pyran-2-yl)oxy]hexa-2,4-dienoate | 115349-61-6

• 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: ethyl (2E,4E)-6-[(tetrahydro-2H-pyran-2-yl)oxy]hexa-2,4-dienoate
• 英文别名: ethyl (2E,4E)-6-(oxan-2-yloxy)hexa-2,4-dienoate
• CAS: 115349-61-6
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: YXEUATXZZQSAJV-PHQNLGIASA-N

物化性质

• 沸点：
  359.3±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (2E,4E)-6-[(tetrahydro-2H-pyran-2-yl)oxy]hexa-2,4-dienoate 在 2,4,6-三甲基吡啶 、 sodium hydride 、 二异丁基氢化铝 、 甲基磺酰氯 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.25h， 生成 (E)-2,9-Bis-methoxycarbonyl-5-methyl-2-[(2E,4E)-6-(tetrahydro-pyran-2-yloxy)-hexa-2,4-dienyl]-dec-5-enedioic acid dimethyl ester
  参考文献：
  名称：

  Ndibwami, Alexis; Lamothe, Serge; Guay, Daniel, Canadian Journal of Chemistry, 1993, vol. 71, # 5, p. 695 - 713

  摘要：

  DOI：
• 作为产物：
  描述：

  顺-4-(四氢吡喃-2-氧)-2-丁烯-1-醇 在 sodium acetate 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 8.5h， 生成 ethyl (2E,4E)-6-[(tetrahydro-2H-pyran-2-yl)oxy]hexa-2,4-dienoate
  参考文献：
  名称：

  Total Synthesis and Antibacterial Testing of the A54556 Cyclic Acyldepsipeptides Isolated fromStreptomyces hawaiiensis

  摘要：

  The first total synthesis of all six known A54556 acyldepsipeptide (ADEP) antibiotics from Streptomyces hawaiiensis is reported. This family of compounds has a unique mechanism of antibacterial action, acting as activators of caseinolytic protease (ClpP). Assembly of the 16-membered depsipeptide core was accomplished via a pentafluorophenyl ester-based macrolactamization strategy. Late stage amine deprotection was carried out under neutral conditions by employing a mild hydrogenolysis strategy, which avoids the formation of undesired ring-opened depsipeptide side products encountered during deprotection of acid-labile protecting groups. The free amines were found to be significantly more reactive toward late stage amide bond formation as compared to the corresponding ammonium salts, giving final products in excellent yields. A thorough NMR spectroscopic analysis of these compounds was carried out to formally assign the structures and to aid with the spectroscopic assignment of ADEP analogues. The identity of two of the structures was confirmed by comparison with biologically produced samples from S. hawaiiensis. An X-ray crystallographic analysis of an ADEP analogue reveals a conformation similar to that found in cocrystal structures of ADEPs with ClpP protease. The degree of antibacterial activity of the different compounds was evaluated in vitro using MIC assays employing both Gram-positive and Gram-negative strains and a fluorescence-based biochemical assay.

  DOI：

  10.1021/np500158q

文献信息

• Berube, Gervais; Deslongchamps, Pierre, Canadian Journal of Chemistry, 1990, vol. 68, # 3, p. 404 - 411
  作者：Berube, Gervais、Deslongchamps, Pierre

  DOI：——

  日期：——
• Synthesis and transannular diels-alder reaction of a 13-membered macrocyclic triene having a tetrasubstituted enol ether as a dienophile
  作者：Gervais Bérubé、Pierre Deslongchamps

  DOI：10.1016/s0040-4039(00)96701-7

  日期：1987.1
• BERUBE, GERVAIS;DESLONGCHAMPS, PIERRE, CAN. J. CHEM., 68,(1990) N, C. 404-411
  作者：BERUBE, GERVAIS、DESLONGCHAMPS, PIERRE

  DOI：——

  日期：——
• BERUBE, GERVAIS;DESLONGCHAMPS, PIERRE, TETRAHEDRON LETT., 28,(1987) N 44, 5255-5258
  作者：BERUBE, GERVAIS、DESLONGCHAMPS, PIERRE

  DOI：——

  日期：——