D-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: D-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran
• 英文别名: 1-[2-[4-[(2S)-3-phenyl-2H-chromen-2-yl]phenoxy]ethyl]piperidine
• 化学式: C₂₈H₂₉NO₂
• 分子量: 411.544
• InChiKey: DBHGMZQRJDUFGS-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 D-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran N-methyl iodide salt
  参考文献：
  名称：

  Resolution, molecular structure and biological activities of the d - and l -enantiomers of potent anti-implantation agent, dl -2-[4-(2-Piperidinoethoxy)phenyl]-3-phenyl-2 H -1-benzopyran

  摘要：

  Compound 1 (DL-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran, CDRI 85/287) a potent anti-estrogen and anti-implantation agent has been successfully resolved into its pure D- and L-enantiomers. Biological studies showed L-enantiomer to be the active form, exhibiting a fivefold higher receptor affinity for the rat uterine cytosolic estrogen receptor, 100% contraceptive efficacy at 1.3 mg/kg dose in single day schedule and 89% inhibition of estradiol induced increase of uterine weight at its contraceptive dose. The absolute stereochemistry determined by X-ray crystallographic analysis showed that the L-enantiomer has 2R configuration at its asymmetric centre.

  DOI：

  10.1016/s0968-0896(99)00131-5
• 作为产物：
  描述：

  D-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran-di-p-toluoyl-D-tartrate 在 sodium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以50 mg的产率得到D-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran
  参考文献：
  名称：

  Resolution, molecular structure and biological activities of the d - and l -enantiomers of potent anti-implantation agent, dl -2-[4-(2-Piperidinoethoxy)phenyl]-3-phenyl-2 H -1-benzopyran

  摘要：

  Compound 1 (DL-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran, CDRI 85/287) a potent anti-estrogen and anti-implantation agent has been successfully resolved into its pure D- and L-enantiomers. Biological studies showed L-enantiomer to be the active form, exhibiting a fivefold higher receptor affinity for the rat uterine cytosolic estrogen receptor, 100% contraceptive efficacy at 1.3 mg/kg dose in single day schedule and 89% inhibition of estradiol induced increase of uterine weight at its contraceptive dose. The absolute stereochemistry determined by X-ray crystallographic analysis showed that the L-enantiomer has 2R configuration at its asymmetric centre.

  DOI：

  10.1016/s0968-0896(99)00131-5