[(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl] N-[(1R)-1-naphthalen-1-ylethyl]carbamate | 777059-73-1

• 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: [(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl] N-[(1R)-1-naphthalen-1-ylethyl]carbamate
• CAS: 777059-73-1
• 化学式: C₃₂H₃₅NO₄
• 分子量: 497.634
• InChiKey: YTCUSVHGIUXNRF-RNWIMVQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl] N-[(1R)-1-naphthalen-1-ylethyl]carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以77%的产率得到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 三氟化硼 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 [(3R)-1,7-bis(4-hydroxyphenyl)heptan-3-yl] N-[(1R)-1-naphthalen-1-ylethyl]carbamate
  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