(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine | 117468-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• 英文别名: methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranoside；methyl-[O⁴,O⁶-((R)-benzylidene)-α-D-erythro-2,3-dideoxy-hexopyranoside]；Methyl-[O⁴,O⁶-((R)-benzyliden)-α-D-erythro-2,3-didesoxy-hexopyranosid]；(2R,4aR,6S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 117468-12-9
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: LASCUIFSNMHEDR-RFQIPJPRSA-N

物化性质

• 熔点：
  199-202 °C
• 沸点：
  364.1±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 barium carbonate 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 (+)-[(2R,3S,6S)-2-cyanomethyl-6-methoxyoxan-3-yl] benzoate
  参考文献：
  名称：

  Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues

  摘要：

  Starting with methyl 4,6-O-benzylidene-alpha -D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O-acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b-18d reveal higher affinity for mu -receptors than for kappa -receptors. The most mu -active compound 18b (K-i = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of mu -receptors.

  DOI：

  10.1002/1521-4184(200109)334:8/9<284::aid-ardp284>3.0.co;2-b
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside 在 甲醇 、 soda lime 、 铂 作用下， 生成 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  3-脱氧d甘露糖。脱氧糖。第十一次沟通

  摘要：

  DOI：

  10.1002/hlca.19460290510

文献信息

• Oxygen–carbon β-bond effects in radical reactions
  作者：Derek H. R. Barton、Wolfgang Hartwig、William B. Motherwell

  DOI：10.1039/c39820000447

  日期：——

  Oxygen bonded to the β-carbon of a carbon radical has a marked stabilising effect; this permits radical reactions not seen except at much higher temperatures in non-oxygenated model compounds.

  与碳自由基的 δ 碳结合的氧具有明显的稳定作用；这使得自由基反应成为可能，除非在温度更高的非氧模型化合物中。
• Jones, Keith; Wood, William W., Journal of the Chemical Society. Perkin transactions I, 1988, p. 999 - 1002
  作者：Jones, Keith、Wood, William W.

  DOI：——

  日期：——
• JONES, KEITH;WOOD, WILLIAM W., J. CHEM. SOC. PERKIN TRANS.,(1988) N 5, 999-1001
  作者：JONES, KEITH、WOOD, WILLIAM W.

  DOI：——

  日期：——
• 3-Desoxy-d-mannose. Desoxyzucker. 11. Mitteilung
  作者：H. R. Bolliger、D. A. Prins

  DOI：10.1002/hlca.19460290510

  日期：——
• Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues
  作者：Georg Höfner、Benedikt Streicher、Bernhard Wünsch

  DOI：10.1002/1521-4184(200109)334:8/9<284::aid-ardp284>3.0.co;2-b

  日期：2001.9

  Starting with methyl 4,6-O-benzylidene-alpha -D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O-acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b-18d reveal higher affinity for mu -receptors than for kappa -receptors. The most mu -active compound 18b (K-i = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of mu -receptors.