(+)-(R)-Isobalfourodin | 478-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+)-(R)-Isobalfourodin
• 英文别名: (-)-(R)-isobalfourodine；(R)-3-hydroxy-9-methoxy-2,2,10-trimethyl-2,3,4,10-tetrahydro-pyrano[2,3-b]quinolin-5-one；(3R)-3-hydroxy-9-methoxy-2,2,10-trimethyl-3,4-dihydropyrano[2,3-b]quinolin-5-one
• CAS: 478-38-6
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: MSDAMDHEPWLWJZ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(R)-Isobalfourodin 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 以95%的产率得到(-)-(R)-ψ-isobalfourodine
  参考文献：
  名称：

  Syntheses and Absolute Configuration Assignments of Mono- and Di-substituted Chiral Quinoline Alkaloids Obtained by Asymmetric Oxidation

  摘要：

  Mono- and di-substituted quinoline, 2-quinolone, dihydrofuroquinoline and dihydropyranoquinoline alkaloids have been synthesised with enantiomeric excess values of > 90%, via asymmetric epoxidation, or asymmetric dihydroxylation of the corresponding alkene precursors. The absolute configurations of isobalfourodine, psi-balfourodine, psi-isobalfourodine, isobalfourodinium methiodide, balfourolone, hydroxylunidine, orixine, nororixine, isopteleflorine, O-acetylisopteleflorine, O-methylhydroxylunium methiodide and hydroxylunine have been rigorously determined by a combination of circular dichroism spectroscopy, ozonolysis, and stereochemical correlation. Of these, the absolute configurations of six alkaloids were previously unknown and six were assigned incorrect configurations in the literature.

  DOI：

  10.3987/com-08-s(d)51
• 作为产物：
  描述：

  (-)-(R)-9-methoxygeibalansine 、 碘甲烷 以88%的产率得到(+)-(R)-Isobalfourodin
  参考文献：
  名称：

  Syntheses and Absolute Configuration Assignments of Mono- and Di-substituted Chiral Quinoline Alkaloids Obtained by Asymmetric Oxidation

  摘要：

  Mono- and di-substituted quinoline, 2-quinolone, dihydrofuroquinoline and dihydropyranoquinoline alkaloids have been synthesised with enantiomeric excess values of > 90%, via asymmetric epoxidation, or asymmetric dihydroxylation of the corresponding alkene precursors. The absolute configurations of isobalfourodine, psi-balfourodine, psi-isobalfourodine, isobalfourodinium methiodide, balfourolone, hydroxylunidine, orixine, nororixine, isopteleflorine, O-acetylisopteleflorine, O-methylhydroxylunium methiodide and hydroxylunine have been rigorously determined by a combination of circular dichroism spectroscopy, ozonolysis, and stereochemical correlation. Of these, the absolute configurations of six alkaloids were previously unknown and six were assigned incorrect configurations in the literature.

  DOI：

  10.3987/com-08-s(d)51

文献信息

• Quinoline alkaloids. Part 17. Mechanism of base-catalysed rearrangement of hydroxyisopropyldihydrofuroquinolones and of dihydrodimethylpyranoquinolones
  作者：Kevin J. James、Michael F. Grundon

  DOI：10.1039/p19790001467

  日期：——

  re-investigation of the stereospecific base-catalysed rearrangement of (+)-(R)-balfourodine (1) and of (+)-(R)isobalfourodine (8) has resulted in improved methods of preparing (+)- and (–)-ψ-balfourodine, in establishing the absolute stereochemistry of the rearrangement products, and in trapping an epoxide intermediate as its methyl ether (9); a new mechanism for rearrangement is proposed.

  对（+）-（R）-balfourodine（1）和（+）-（R）异balfourodine（8）的立体特异性碱催化重排的重新研究导致制备（+）-和（ - ） - ψ -balfourodine，在建立重排产物的绝对立体化学，而在捕获作为其甲基醚（9）的中间体环氧化物; 提出了一种新的重排机制。