(+)-Orixin | 1162079-70-0

• 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: (+)-Orixin
• 英文别名: (S)-1-(6,8-dimethoxy-[1,3]dioxolo[4,5-h]quinolin-7-yl)-3-methyl-butane-2,3-diol；(+)-orixine；(2S)-1-(6,8-dimethoxy-[1,3]dioxolo[4,5-h]quinolin-7-yl)-3-methylbutane-2,3-diol
• CAS: 1162079-70-0
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: UEHVFWBKXUSZEQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-Orixin 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 生成 Dihydro-N-methyl-orixidin
  参考文献：
  名称：

  Alkaloids of the Root-bark of <I>Orixa japonica</I> THUNB. XI. The Structures of Orixidine and Orixidinine

  摘要：

  讨论了奥利昔啶和奥利昔啶的结构，并确定了它们的 2(1H)-喹啉酮结构，奥利昔啶和奥利昔啶都是奥利昔啶的去甲基化产物。据推测，奥利昔啶和奥利昔啶的结构应分别为(IV)和(XIII)，而(XIV)的异构转化产物异-N-甲基奥利昔啶的结构为(XVI)。

  DOI：

  10.1248/cpb.10.792
• 作为产物：
  描述：

  2,4-Dimethoxy-3-(3-methyl-buten-(2)-yl)-7,8-methylendioxy-chinolin 在 四氧化锇 、 甲基磺酰胺 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 potassium ferricyanide 作用下， 以 水 、 叔丁醇 为溶剂， 生成 (+)-Orixin
  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

• Terasaka, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1931, vol. 51, p. 707,715; dtsch. Ref. S. 99, 102
  作者：Terasaka

  DOI：——

  日期：——
• Terasaka,M., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 523 - 529
  作者：Terasaka,M.

  DOI：——

  日期：——
• Terasaka, Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 946,947
  作者：Terasaka

  DOI：——

  日期：——
• 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.
• Alkaloids of the Root-bark of &lt;I&gt;Orixa japonica&lt;/I&gt; THUNB. XI. The Structures of Orixidine and Orixidinine
  作者：Kazuko Narahashi

  DOI：10.1248/cpb.10.792

  日期：——

  The structures of orixidine and orixidinine, both demethylation products of orixine, were discussed and their 2(1H)-quinolone structures were established. It is assumed that orixidine and orixidinine should have structures (IV) and (XIII), respectively, while that of the isomeric transformation product of (XIV), iso-N-methylorixidinine, structure (XVI).

  讨论了奥利昔啶和奥利昔啶的结构，并确定了它们的 2(1H)-喹啉酮结构，奥利昔啶和奥利昔啶都是奥利昔啶的去甲基化产物。据推测，奥利昔啶和奥利昔啶的结构应分别为(IV)和(XIII)，而(XIV)的异构转化产物异-N-甲基奥利昔啶的结构为(XVI)。