(1'S,2S,4'R)-5,7-dimethoxy-2',2'-dimethylspiro[3H-chromene-2,3'-bicyclo[2.2.1]heptane]-4-one | 114976-80-6

• 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: (1'S,2S,4'R)-5,7-dimethoxy-2',2'-dimethylspiro[3H-chromene-2,3'-bicyclo[2.2.1]heptane]-4-one
• CAS: 114976-80-6
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: KFMYQWAIFQBFQR-CRTZDJKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1'S,2S,4'R)-5,7-dimethoxy-2',2'-dimethylspiro[3H-chromene-2,3'-bicyclo[2.2.1]heptane]-4-one 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 pyridinium hydrobromide perbromide 、 氢气 、 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 7.5h， 生成 [(1'S,2S,4R,4'R)-6-(hydroxymethyl)-5,7-dimethoxy-2',2'-dimethyl-4-(2-methylpropyl)spiro[3,4-dihydrochromene-2,3'-bicyclo[2.2.1]heptane]-8-yl]methanol
  参考文献：
  名称：

  Robustadials. 3. Total synthesis of camphane analogs

  摘要：

  DOI：

  10.1021/jo00251a006
• 作为产物：
  描述：

  2-[(1R,4S)-3,3-Dimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-1-(2,4,6-trimethoxy-phenyl)-ethanone 在 三氯化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (1'S,2S,4'R)-5,7-dimethoxy-2',2'-dimethylspiro[3H-chromene-2,3'-bicyclo[2.2.1]heptane]-4-one
  参考文献：
  名称：

  Robustadials. 3. Total synthesis of camphane analogs

  摘要：

  DOI：

  10.1021/jo00251a006

文献信息

• The Synthesis of (-)-Robustadial A and Some Analogues.
  作者：Inger Reidun Aukrust、Lars Skattebøl、Otto Dahl、Georg Hvistendahl、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0132

  日期：——

  The naturally occurring chroman derivative, robustadial A, and several analogues have been prepared by a four-step synthesis starting from phloroglucinol. The synthetic scheme involves as the first step a Friedel-Crafts condensation of an alpha,beta-unsaturated acid derivative with phloroglucinol to the corresponding chromanone. The isobutyl group at the 4-position was introduced with methallylzine bromide followed by hydrogenation, carried out as a one-pot reaction. Finally, both aldehyde functions were attached using dichloromethyl methyl ether and titanium tetrachloride. Optically pure 6,6-dimethylbicyclo[3.1.1]heptan-2-ylidene-acetic acid, needed for the synthesis of robustadial, was prepared from (-)-nopol by two consecutive oxidations in 77% overall yield.
• MAZZA, SAMUEL M.;LAL, KASTURI;SALOMON, ROBERT G., J. ORG. CHEM., 53,(1988) N 16, C. 3681-3688
  作者：MAZZA, SAMUEL M.、LAL, KASTURI、SALOMON, ROBERT G.

  DOI：——

  日期：——