(S)-1-(6,8-二甲氧基-1,3-二氧杂环戊并[4,5-h]喹啉-7-基)-3-甲基-2,3-丁二醇 | 17232-53-0

• 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
• 中文名称: (S)-1-(6,8-二甲氧基-1,3-二氧杂环戊并[4,5-h]喹啉-7-基)-3-甲基-2,3-丁二醇
• 英文名称: (+)-orixine
• 英文别名: (2R)-1-(6,8-dimethoxy-[1,3]dioxolo[4,5-h]quinolin-7-yl)-3-methylbutane-2,3-diol
• CAS: 17232-53-0
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: UEHVFWBKXUSZEQ-GFCCVEGCSA-N

物化性质

• 沸点：
  491.6±40.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)
• 熔点：
  152.5 °C

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

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (S)-1-(6,8-二甲氧基-1,3-二氧杂环戊并[4,5-h]喹啉-7-基)-3-甲基-2,3-丁二醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以1.4 mg的产率得到(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-(6,8-dimethoxy-[1,3]dioxolo[4,5-h]quinolin-7-ylmethyl)-2-hydroxy-2-methyl-propyl ester
  参考文献：
  名称：

  Absolute Stereochemistry of (-)-Preorixine and Related Compounds.

  摘要：

  (-)-preorixine的C-2'位点的绝对立体化学结构被认为是多种喹啉生物合成前体的重要结构，通过结合其化学转化和扩展的Mosher方法，将其确定为R。(+)-orixine的C-2'位点的立体化学结构也被确定为R，从而确定当(-)-preorixine转化为(+)-orixine时不会发生反转。

  DOI：

  10.1248/cpb.44.1885
• 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 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium ferricyanide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以73%的产率得到(S)-1-(6,8-二甲氧基-1,3-二氧杂环戊并[4,5-h]喹啉-7-基)-3-甲基-2,3-丁二醇
  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

• Funayama, Shinji; Kageyama, Takahiro; Murata, Kiyoshi, Heterocycles, 1993, vol. 35, # 2, p. 607 - 610
  作者：Funayama, Shinji、Kageyama, Takahiro、Murata, Kiyoshi、Adachi, Michiko、Nozoe, Shigeo

  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.
• Absolute Stereochemistry of (-)-Preorixine and Related Compounds.
  作者：Shinji FUNAYAMA、Kiyoshi MURATA、Shigeo NOZOE

  DOI：10.1248/cpb.44.1885

  日期：——

  The absolute stereochemistry of the C-2' position of (-)-preorixine, postulated to be an important biosynthetic precursor of various quinoline alkaloids, was assigned as R by the combination of its chemical transformation and the extended Mosher method. The stereochemistry of the C-2' position of (+)-orixine was also concluded to be R, establishing taht no inversion occurred when (-)-preorixine was transformed into (+)-orixine.

  (-)-preorixine的C-2'位点的绝对立体化学结构被认为是多种喹啉生物合成前体的重要结构，通过结合其化学转化和扩展的Mosher方法，将其确定为R。(+)-orixine的C-2'位点的立体化学结构也被确定为R，从而确定当(-)-preorixine转化为(+)-orixine时不会发生反转。