(-)-(3S,4S)-3,4-epoxy-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-[2H]-pyrano[2,3-b]quinoline | 1162079-53-9

• 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: (-)-(3S,4S)-3,4-epoxy-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-[2H]-pyrano[2,3-b]quinoline
• 英文别名: (11S,13S)-4,9-dimethoxy-14,14-dimethyl-12,15-dioxa-2-azatetracyclo[8.5.0.03,8.011,13]pentadeca-1,3(8),4,6,9-pentaene
• CAS: 1162079-53-9
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: QBDCCEXJJPHTFO-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(3S,4S)-3,4-epoxy-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-[2H]-pyrano[2,3-b]quinoline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以0.121 g的产率得到9-methoxygeibalansine
  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：

  5,9-dimethoxy-2,2-dimethyl-[2H]-pyrano[2,3-b]quinoline 在 sodium hypochlorite 、 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine 、 manganese(II) acetate 、 lithium chloride 作用下， 以 二氯甲烷 、 水 为溶剂， 以20%的产率得到(-)-(3S,4S)-3,4-epoxy-3,4-dihydro-5,9-dimethoxy-2,2-dimethyl-[2H]-pyrano[2,3-b]quinoline
  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

• Syntheses and Absolute Configuration Assignments of Mono- and Di-substituted Chiral Quinoline Alkaloids Obtained by Asymmetric Oxidation
  作者：Derek R. Boyd、Narain D. Sharma、Pui L. Loke、Stephen A. Barr

  DOI：10.3987/com-08-s(d)51

  日期：——

  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.