edulan I | 162488-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: edulan I
• 英文别名: (2R,8aS)-2,5,5,8a-tetramethyl-3,6-dihydro-2H-chromene
• CAS: 162488-95-1
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: HUXGOQHTDHIKSS-MFKMUULPSA-N

物化性质

• 沸点：
  256.3±39.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one 在 platinum(IV) oxide 、 palladium/alumina 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 氢气 、 溴化乙啶 、 4-甲基苯磺酸吡啶 、 magnesium 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 为溶剂， 反应 32.5h， 生成 edulan I
  参考文献：
  名称：

  Weyerstahl, Peter; Meisel, Thomas, Liebigs Annalen der Chemie, 1994, # 4, p. 415 - 428

  摘要：

  DOI：

文献信息

• Chiral syntheses of edulans I, II and dihydroedulans I, II and absolute configurations of edulans I, II
  作者：Toshio Honda、Akira Yamauchi、Masayoshi Tsubuki、Takeshi Matsumoto

  DOI：10.1016/s0957-4166(97)00055-4

  日期：1997.3

  Enantiospecific syntheses of (+)- and (−)-edulans I, II and (−)-dihydroedulans I, II, starting from (R)- and (S)-3-hydroxybutyric acid methyl esters, allowed the determination of the absolute configurations of edulans I, II.

  从（R）-和（S）-3-羟基丁酸甲酯开始的（+）-和（-）-伊杜兰I，II和（-）-二氢伊杜兰I，II的对映体特异性合成可以确定绝对值edulans I，II的配置。
• Synthesis and Enantiodifferentiation of Isomeric 3,5,6,8a-Tetrahydro-2,5,5,8a-tetramethyl-2H-1-benzopyrans (Edulans I and II)
  作者：Gertraut Schmidt、Gerhard Full、Peter Winterhalter、Peter Schreier

  DOI：10.1021/jf00049a034

  日期：1995.1

  The benzopyran derivatives 1a-d were prepared in a biomimetic-type reaction from their natural precursor 3-hydroxy-retro-alpha-ionol (6) which was available from alpha-ionol by tert-butyl chromate oxidation, reduction with NaBH4, and subsequent rearrangement of the 7,8 double bond. The so-obtained geometrical isomers 8-oxo-retro-alpha-ionol 4a/b were separated by preparative and analytical multilayer coil countercurrent chromatography. The racemic 3-oxo-retro-alpha-ionol 4a was esterified with (R)-(-)-2-phenylpropionic acid, and the resulting diastereomeric esters (5a/b) were isolated in pure form (de 90%) by preparative HPLC. Configuration at C-9 was determined by H-1 NMR spectroscopy. The isomeric diols 6a/b obtained from esters 5a/b by LiAlH4 reductive cleavage were subjected to thermal treatment (simultaneous distillation extraction), yielding two pairs of diastereomeric edulans (1a/b and 1c/d) which were subsequently obtained in optically pure form by analytical HPLC. The absolute configuration at C-8a was established by NOE experiments. Using on-line coupled multidimensional gas chromatography-mass spectrometry [DB-Wax/heptakis-(2,6-di-O-methyl-3-O-pentyl)-beta- cyclodextrin] with selected ion monitoring mode, enantiodifferentiation of 1a-d in a number of natural sources revealed predominance of the 2S enantiomers.
• Etoh, Hideo; Ina, Kazuo; Iguchi, Masanobu, Agricultural and Biological Chemistry, <hi>1980</hi>, vol. 44, # 12, p. 2871 - 2876
  作者：Etoh, Hideo、Ina, Kazuo、Iguchi, Masanobu

  DOI：——

  日期：——

表征谱图