(R)-N-benzyl-3-benzyloxymethylmorpholine | 205242-60-0

• 物质功能分类: 材料化学 - 发光材料
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-N-benzyl-3-benzyloxymethylmorpholine
• 英文别名: (R)-4-benzyl-2-((benzyloxy)methyl)morpholine；(2R)-4-benzyl-2-(phenylmethoxymethyl)morpholine
• CAS: 205242-60-0
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: YIUOMOUSMWDPKQ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (R)-N-benzyl-3-benzyloxymethylmorpholine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 55.0~60.0 ℃ 、101.32 kPa 条件下， 反应 4.0h， 以52%的产率得到(R)-吗啉-2-基甲醇盐酸盐
  参考文献：
  名称：

  (R)-(+)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine Methanesulfonate:  A New Selective Rat 5-Hydroxytryptamine_1B Receptor Antagonist

  摘要：

  In the search for new 5-hydroxytryptamine (5-HT) receptor antagonists it was found that the compound (R)-(+)-2-[[[3-(morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine methanesulfonate, (R)-25, is a selective rat 5-hydroxytryptamine(1B) (r5-HT1B) receptor antagonist. The binding profile showed a 13-fold preference for r5-HT1B (K-i = 47 +/- 5 nM; n = 3) vs bovine 5-HT1B (K-i = 630 nM; n = 1) receptors. The compound had very low affinity for other monoaminergic receptors examined. The r5-HT1B receptor antagonism was demonstrated by the potentiation of the K+-stimulated release of [H-3]-5-HT from superfused rat brain slices in vitro, an effect that was antagonized by addition of 5-HT to the superfusion fluid. (R)-25 at 20 mg/kg sc enhanced the 5-HT turnover in four rat brain regions (hypothalamus, hippocampus, striatum, and frontal cortex) with about 40% measured as the 5-HTP accumulation after decarboxylase inhibition with 3-hydroxybenzylhydrazine. At 3 mg/kg sc (R)-25 produced a significant increase in the number of wet dog shakes in rats, a 5-HT2A/5-HT2C response that was abolished by depletion of 5-HT after pretreatment with the tryptophan hydroxylase inhibitor p-chlorophenylalanine. These observations show that (R)-25, by inhibiting terminal r5-HT1B autoreceptors, increases the 5-HT turnover and the synaptic concentration of 5-HT.

  DOI：

  10.1021/jm970806i
• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 在 甲醇 、 lithium aluminium tetrahydride 、 sodium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 72.17h， 生成 (R)-N-benzyl-3-benzyloxymethylmorpholine
  参考文献：
  名称：

  (R)-(+)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine Methanesulfonate:  A New Selective Rat 5-Hydroxytryptamine_1B Receptor Antagonist

  摘要：

  In the search for new 5-hydroxytryptamine (5-HT) receptor antagonists it was found that the compound (R)-(+)-2-[[[3-(morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine methanesulfonate, (R)-25, is a selective rat 5-hydroxytryptamine(1B) (r5-HT1B) receptor antagonist. The binding profile showed a 13-fold preference for r5-HT1B (K-i = 47 +/- 5 nM; n = 3) vs bovine 5-HT1B (K-i = 630 nM; n = 1) receptors. The compound had very low affinity for other monoaminergic receptors examined. The r5-HT1B receptor antagonism was demonstrated by the potentiation of the K+-stimulated release of [H-3]-5-HT from superfused rat brain slices in vitro, an effect that was antagonized by addition of 5-HT to the superfusion fluid. (R)-25 at 20 mg/kg sc enhanced the 5-HT turnover in four rat brain regions (hypothalamus, hippocampus, striatum, and frontal cortex) with about 40% measured as the 5-HTP accumulation after decarboxylase inhibition with 3-hydroxybenzylhydrazine. At 3 mg/kg sc (R)-25 produced a significant increase in the number of wet dog shakes in rats, a 5-HT2A/5-HT2C response that was abolished by depletion of 5-HT after pretreatment with the tryptophan hydroxylase inhibitor p-chlorophenylalanine. These observations show that (R)-25, by inhibiting terminal r5-HT1B autoreceptors, increases the 5-HT turnover and the synaptic concentration of 5-HT.

  DOI：

  10.1021/jm970806i

文献信息

• Synthesis of (R)- and (S)-Oxymethylmorpholine Derivatives
  作者：Chi-Wan Lee、Seok Jong Lee

  DOI：10.1080/00397910008087353

  日期：2000.2

  (S)-N-benzyl-3-tert-butyldiphenylsilyloxymethylmorpholine and (R)-N-benzyl-3-benzyloxymethylmorpholine are synthesized starting from (R)-1-benzylglycerol.
• (<i>R</i>)-(+)-2-[[[3-(Morpholinomethyl)-2<i>H</i>-chromen-8-yl]oxy]methyl]morpholine Methanesulfonate:  A New Selective Rat 5-Hydroxytryptamine_1B Receptor Antagonist
  作者：Stefan Berg、Lars-Gunnar Larsson、Lucy Rényi、Svante B. Ross、Seth-Olof Thorberg、Gun Thorell-Svantesson

  DOI：10.1021/jm970806i

  日期：1998.5.1

  In the search for new 5-hydroxytryptamine (5-HT) receptor antagonists it was found that the compound (R)-(+)-2-[[[3-(morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine methanesulfonate, (R)-25, is a selective rat 5-hydroxytryptamine(1B) (r5-HT1B) receptor antagonist. The binding profile showed a 13-fold preference for r5-HT1B (K-i = 47 +/- 5 nM; n = 3) vs bovine 5-HT1B (K-i = 630 nM; n = 1) receptors. The compound had very low affinity for other monoaminergic receptors examined. The r5-HT1B receptor antagonism was demonstrated by the potentiation of the K+-stimulated release of [H-3]-5-HT from superfused rat brain slices in vitro, an effect that was antagonized by addition of 5-HT to the superfusion fluid. (R)-25 at 20 mg/kg sc enhanced the 5-HT turnover in four rat brain regions (hypothalamus, hippocampus, striatum, and frontal cortex) with about 40% measured as the 5-HTP accumulation after decarboxylase inhibition with 3-hydroxybenzylhydrazine. At 3 mg/kg sc (R)-25 produced a significant increase in the number of wet dog shakes in rats, a 5-HT2A/5-HT2C response that was abolished by depletion of 5-HT after pretreatment with the tryptophan hydroxylase inhibitor p-chlorophenylalanine. These observations show that (R)-25, by inhibiting terminal r5-HT1B autoreceptors, increases the 5-HT turnover and the synaptic concentration of 5-HT.