1,7-Bis[4-(oxan-2-yloxy)phenyl]heptan-3-ol | 777059-70-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,7-Bis[4-(oxan-2-yloxy)phenyl]heptan-3-ol
• CAS: 777059-70-8
• 化学式: C₂₉H₄₀O₅
• 分子量: 468.634
• InChiKey: PBEIZYOBFYDQQW-UHFFFAOYSA-N

物化性质

• 沸点：
  639.1±55.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,7-Bis[4-(oxan-2-yloxy)phenyl]heptan-3-ol 在 lithium aluminium tetrahydride 、 三氟化硼 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 Centrolobol; (R)-(-)-1,7-双对羟基苯基-3-庚醇
  参考文献：
  名称：

  Identification of Centrolobol as the Platyphylloside Metabolite Responsible for the Observed Effect on in Vitro Digestibility of Hay

  摘要：

  Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4'-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers of 1,7-bis(4'-hydroxyphenyl)-3-heptanol (centrolobol) and 1,7-bis(4-hydroxyphenyl)heptane (platyphyllane) were synthesized and tested regarding digestibility inhibition in vitro in cow rumen fluid. All compounds tested induced a decreased digestion. Centrolobol was found to be the metabolite causing the observed effect, and (R)-centrolobol was found to be the enantiomer formed in the rumen liquor in vitro.

  DOI：

  10.1021/jf040135e
• 作为产物：
  描述：

  2-对溴苯氧基四氢吡喃 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 1,7-Bis[4-(oxan-2-yloxy)phenyl]heptan-3-ol
  参考文献：
  名称：

  Identification of Centrolobol as the Platyphylloside Metabolite Responsible for the Observed Effect on in Vitro Digestibility of Hay

  摘要：

  Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4'-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers of 1,7-bis(4'-hydroxyphenyl)-3-heptanol (centrolobol) and 1,7-bis(4-hydroxyphenyl)heptane (platyphyllane) were synthesized and tested regarding digestibility inhibition in vitro in cow rumen fluid. All compounds tested induced a decreased digestion. Centrolobol was found to be the metabolite causing the observed effect, and (R)-centrolobol was found to be the enantiomer formed in the rumen liquor in vitro.

  DOI：

  10.1021/jf040135e

文献信息

• Identification of Centrolobol as the Platyphylloside Metabolite Responsible for the Observed Effect on in Vitro Digestibility of Hay
  作者：Kerstin Sunnerheim、Katharina Bratt

  DOI：10.1021/jf040135e

  日期：2004.9.1

  Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4'-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers of 1,7-bis(4'-hydroxyphenyl)-3-heptanol (centrolobol) and 1,7-bis(4-hydroxyphenyl)heptane (platyphyllane) were synthesized and tested regarding digestibility inhibition in vitro in cow rumen fluid. All compounds tested induced a decreased digestion. Centrolobol was found to be the metabolite causing the observed effect, and (R)-centrolobol was found to be the enantiomer formed in the rumen liquor in vitro.