ethyl 7,9-dioxo-8-methyldecanoate | 730971-94-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 7,9-dioxo-8-methyldecanoate
• 英文别名: ethyl 8-methyl-7,9-dioxodecanoate
• CAS: 730971-94-5
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: ZJZUJPMVPPGOON-UHFFFAOYSA-N

物化性质

• 沸点：
  341.4±22.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 7,9-dioxo-8-methyldecanoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四(三苯基膦)钯 氢氧化钾 、 lithium hydroxide 、 copper(l) iodide 、 ammonium cerium(IV) nitrate 、 三丁基膦 、 四丁基氟化铵 、 碘 、 sodium acetate 、 potassium hydrogencarbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 一氯丙酮 、 potassium iodide 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 水 、 溶剂黄146 、 二乙胺 、 苯 为溶剂， 反应 57.84h， 生成 methyl 6-[5-[(Z)-(3-ethyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-2-[4-[5-[(Z)-(3-ethyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-3-(6-methoxy-6-oxohexyl)-4-methyl-1H-pyrrol-2-yl]buta-1,3-diynyl]-4-methyl-1H-pyrrol-3-yl]hexanoate
  参考文献：
  名称：

  Novel Linear Tetrapyrroles: Hydrogen Bonding in Diacetylenic Bilirubins

  摘要：

  Bilirubin congeners with dipyrrinones conjoined to a diaceteylene unit (-Cequivalent toC-Cequivalent toC-) rather than to -CH2- were synthesized and examined spectroscopically. This new class of rubrified linear tetrapyrroles cannot easily fold or bend in the middle, but the dipyrrinones can rotate independently about the diacetylene unit. Thus, unlike bilirubin, which is bent in the middle and has a ridge-tile shape, the diacetylene unit orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding between the dipyrrinones and opposing carboxylic acids preserves a twisted linear molecular shape when the usual propionic acids are replaced by hexanoic. In a bis-hexanoic acid rubin, the extended planes of the dipyrrinones intersect along the -(Cequivalent toC)(2)- axis at an angle of 102degrees for the conformation stabilized by intramolecular hydrogen bonding. With propionic acid chains, however, neither CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and the energy-minimum conformation of this linear pigment, shows nearly co-planar dipyrrinones, with an intersection of an angle of similar to180degrees of the extended planes of the dipyrrinones. Spectroscopic evidence for such linearized and twisted (bis-hexanoic) and planar (bis-propionic) structures comes from the pigments' NMR spectral data and their exciton UV-Vis and induced circular dichroism spectra.

  DOI：

  10.1007/s00706-003-0157-3
• 作为产物：
  描述：

  庚二酸单乙酯钾盐 在 草酰氯 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 ethyl 7,9-dioxo-8-methyldecanoate
  参考文献：
  名称：

  Novel Linear Tetrapyrroles: Hydrogen Bonding in Diacetylenic Bilirubins

  摘要：

  Bilirubin congeners with dipyrrinones conjoined to a diaceteylene unit (-Cequivalent toC-Cequivalent toC-) rather than to -CH2- were synthesized and examined spectroscopically. This new class of rubrified linear tetrapyrroles cannot easily fold or bend in the middle, but the dipyrrinones can rotate independently about the diacetylene unit. Thus, unlike bilirubin, which is bent in the middle and has a ridge-tile shape, the diacetylene unit orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding between the dipyrrinones and opposing carboxylic acids preserves a twisted linear molecular shape when the usual propionic acids are replaced by hexanoic. In a bis-hexanoic acid rubin, the extended planes of the dipyrrinones intersect along the -(Cequivalent toC)(2)- axis at an angle of 102degrees for the conformation stabilized by intramolecular hydrogen bonding. With propionic acid chains, however, neither CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and the energy-minimum conformation of this linear pigment, shows nearly co-planar dipyrrinones, with an intersection of an angle of similar to180degrees of the extended planes of the dipyrrinones. Spectroscopic evidence for such linearized and twisted (bis-hexanoic) and planar (bis-propionic) structures comes from the pigments' NMR spectral data and their exciton UV-Vis and induced circular dichroism spectra.

  DOI：

  10.1007/s00706-003-0157-3