(4R,4aS,7S,7aR,12bS)-4a,7-dihydroxy-9-methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-carbaldehyde | 1108715-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (4R,4aS,7S,7aR,12bS)-4a,7-dihydroxy-9-methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-carbaldehyde
• CAS: 1108715-09-8
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: YSUCPICQAHMRSI-HWDJUHOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  79.23
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,4aS,7S,7aR,12bS)-4a,7-dihydroxy-9-methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-carbaldehyde 在 sodium acetate 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. 1: Synthesis of triplet drugs with morphinan skeletons

  摘要：

  We synthesized symmetrical and nonsymmetrical triplet drugs with 1,3,5-trioxazatriquinane skeletons. The isolation of key intermediates, oxazoline dimers, made it possible to effectively produce nonsymmetrical triplets. Among the synthesized triplets, KNT-93, composed of three identical opioid mu receptor agonists, showed dose-dependent antinociception via the mu receptor. The effect was 56-fold more potent than that of morphine, a representative mu agonist. The profound analgesic effect induced by KNT-93 might result from simultaneous occupation of three mu opioid receptors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.134
• 作为产物：
  描述：

  (4R,4aS,7S,7aR,12bS)-7-(dimethoxymethyl)-9-methoxy-3-methyl-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7-diol 在 盐酸 作用下， 以 水 为溶剂， 生成 (4R,4aS,7S,7aR,12bS)-4a,7-dihydroxy-9-methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-carbaldehyde
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. 1: Synthesis of triplet drugs with morphinan skeletons

  摘要：

  We synthesized symmetrical and nonsymmetrical triplet drugs with 1,3,5-trioxazatriquinane skeletons. The isolation of key intermediates, oxazoline dimers, made it possible to effectively produce nonsymmetrical triplets. Among the synthesized triplets, KNT-93, composed of three identical opioid mu receptor agonists, showed dose-dependent antinociception via the mu receptor. The effect was 56-fold more potent than that of morphine, a representative mu agonist. The profound analgesic effect induced by KNT-93 might result from simultaneous occupation of three mu opioid receptors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.134

文献信息

• Novel Synthesis of a 1,3,5-Trioxazatriquinane Skeleton Using a Nitrogen Clamp
  作者：Hiroshi Nagase、Akio Watanabe、Masaya Harada、Mayumi Nakajima、Ko Hasebe、Hidenori Mochizuki、Kenji Yoza、Hideaki Fujii

  DOI：10.1021/ol8024988

  日期：2009.2.5

  An α-hydroxyaldehyde derived from naltrexone was converted to an oxazoline dimer with ammonium chloride and sodium acetate in MeOH under reflux. The resulting dimer was treated with dl-camphorsulfonic acid in CHCl3 to give the trimer. The method for trimer synthesis was also applied to general α-hydroxyaldehydes to afford trimers in good yield.

  用氯化铵和乙酸钠在MeOH中的溶液在回流下将衍生自纳曲酮的α-羟醛转化为恶唑啉二聚体。将所得的二聚体在CHCl 3中用dl-樟脑磺酸处理，得到三聚体。三聚体合成的方法也适用于一般的α-羟基醛，以良好的收率得到三聚体。