orixalone D

• 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: orixalone D
• 英文别名: Heuvgodfdjkjtp-wcqyabfasa-；(3R,4S)-3,4-dihydroxy-2,2,6-trimethyl-3,4-dihydropyrano[3,2-c]quinolin-5-one
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: HEUVGODFDJKJTP-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 在 二甲基二环氧乙烷 、 ytterbium(III) triflate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 12.0h， 生成 orixalone D
  参考文献：
  名称：

  Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products

  摘要：

  An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-0-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.022

文献信息

• Efficient Synthesis of Substituted Pyranoquinolinones from 2,4-Dihydroxy­quinoline: Total Synthesis of Zanthosimuline, <b><i>cis</i></b>-3<b>′</b>,4<b>′</b>-Dihydroxy-3<b>′</b>,4<b>′</b>-di­hydroflindersine, and Orixalone D
  作者：Yong Lee、Xue Wang

  DOI：10.1055/s-2007-983893

  日期：2007.10

  A convenient and efficient synthesis of pyranoquinoli-nones was achieved using the ethylenediamine diacetate catalyzed reactions of 2,4-dihydroxyquinoline and a variety of α,β-unsaturated aldehydes in good yield. The key feature of these reactions is the formal [3+3] cycloaddition. This new methodology was applied successfully to the total synthesis of naturally occurring pyranoquinolinone alkaloids

  使用乙二胺二乙酸酯催化的 2,4-二羟基喹啉和多种 α,β-不饱和醛的反应以良好的收率实现了一种方便高效的吡喃喹啉酮合成。这些反应的关键特征是正式的 [3+3] 环加成。这种新方法成功地应用于天然存在的吡喃喹啉酮生物碱、zanthosimuline、CIS-3',4'-dihydroxy-3',4'-dihydroflindersine 和 orixalone D 的全合成。
• Total Syntheses of Pyranoquinoline Alkaloids:  Simulenoline, Huajiaosimuline, and (±)-7-Demethoxyzanthodioline
  作者：Michael J. McLaughlin、Richard P. Hsung

  DOI：10.1021/jo001368h

  日期：2001.2.1
• Brown et al., Australian Journal of Chemistry, 1954, vol. 7, p. 348,369
  作者：Brown et al.

  DOI：——

  日期：——
• Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products
  作者：Xue Wang、Yong Rok Lee

  DOI：10.1016/j.tetlet.2007.07.022

  日期：2007.9

  An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-0-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin. (c) 2007 Elsevier Ltd. All rights reserved.

表征谱图