(+)-[(2R,3S,6S)-2-cyanomethyl-6-methoxyoxan-3-yl] benzoate | 330953-54-3

• 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: (+)-[(2R,3S,6S)-2-cyanomethyl-6-methoxyoxan-3-yl] benzoate
• 英文别名: (+)-(2R,3S,6S)-2-cyanomethyl-6-methoxyoxan-3-yl benzoate；[(2R,3S,6S)-2-(cyanomethyl)-6-methoxyoxan-3-yl] benzoate
• CAS: 330953-54-3
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: NADCNRBYVQWKQI-MJBXVCDLSA-N

物化性质

• 沸点：
  432.5±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-[(2R,3S,6S)-2-cyanomethyl-6-methoxyoxan-3-yl] benzoate 在 镍 丁二酰亚胺 、 sodium hydroxide 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 40.5h， 生成 (+)-benzyl N-{2-[(2R,6S)-6-methoxy-5,6-dihydro-2H-pyran-2-yl]ethyl}carbamate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure Morphan Analogues from α-D-Glucose

  摘要：

  DOI：

  10.1002/1099-0690(200101)2001:1<115::aid-ejoc115>3.3.co;2-6
• 作为产物：
  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

文献信息

• 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.
• Synthesis of Enantiomerically Pure Morphan Analogues from α-D-Glucose
  作者：Benedikt Streicher、Bernhard Wünsch

  DOI：10.1002/1099-0690(200101)2001:1<115::aid-ejoc115>3.3.co;2-6

  日期：2001.1