2,3-dihydro-8-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one | 15496-18-1

• 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: 2,3-dihydro-8-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one
• 英文别名: 8-Methoxy-2.2-dimethylchroman-4-on；8-methoxy-2,2-dimethyl-chroman-4-one；8-Methoxy-2,2-dimethylchroman-4-one；8-methoxy-2,2-dimethyl-3H-chromen-4-one
• CAS: 15496-18-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: XPVAFZFSGRBVBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (8-methoxy-2,2-dimethyl-4-oxo-3H-chromen-7-yl) N,N-diethylcarbamimidate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以81%的产率得到2,3-dihydro-8-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Modification of Hydroxybenzopyranoids: Facile Deoxygenation of 2,2-Dimethyl-7-hydroxy-4-chromanones and a New Approach to Their Novel Mercapto Analogs

  摘要：

  A facile deoxygenation of a systematic series of substituted 2,2-dimethyl-7-hydroxy-4-chromanones via their sulfonate, isourea, and thiocarbamate derivatives is reported. The synthesis of novel 2,2-dimethyl-7-mercapto-4-chromanones has been accomplished by the hydrolysis of the corresponding thiocarbamates. The scope and limitations of different deoxygenation procedures in the case of these hydroxybenzopyranoids are also presented.

  DOI：

  10.1021/jo00100a038

文献信息

• Fries rearrangement of methoxyphenyl 3-methylbut-2-enoates
  作者：F. Camps、J. Coll、O. Colomina、A. Messeguer

  DOI：10.1002/jhet.5570220229

  日期：1985.3

  Fries rearrangement of 2-, 3- and 4-methoxyphenyl 3-methylbut-2-enoates 3-5 in methanesulfonic acid, polyphosphoric acid, aluminum chloride and under photochemical conditions have been studied. The outcome of the reactions was determined by the substitution pattern in the starting products and the reaction conditions used. Under Lewis acid catalysis, acylation accounted for the major components of

  已经研究了在甲磺酸，多磷酸，氯化铝中和在光化学条件下2-，3-和4-甲氧基苯基3-甲基丁-2-烯酸酯3-5的薯条重排。反应的结果取决于起始产物中的取代方式和所用的反应条件。下路易斯酸催化，酰化占反应混合物的主要成分，导致茚满酮和2,3-二氢4的形成ħ分别-1-苯并吡喃-4-酮在的情况下ø -和米-酯3和5，而烷基化得到二氢香豆素是对酯5的优选途径。另一方面，在所有情况下，o-酰化是光化学重排中的主要反应过程。
• Facile Deoxygenation of Hydroxylated Flavonoids by Palladium-Catalysed Reduction of its Triflate Derivatives
  作者：József Kövér、Sándor Antus

  DOI：10.1515/znb-2005-0716

  日期：2005.7.1

  An efficient procedure to deoxygenate hydroxy substituted flavonoids, isoflavonoids and related compounds via their trifluoromethanesulfonates is presented. Their reduction with formic acid in the presence of a catalytic amount of palladium acetate, triethylamine and 1,3-bis(diphenylphosphanyl) propane (dppp) in DMF results in their des-hydroxy derivatives without affecting other functional groups.

  通过使用三氟甲磺酸盐，以催化量的乙酸钯、三乙胺和1,3-双(二苯基膦基)丙烷（dppp）在DMF中，将含羟基的黄酮类化合物、异黄酮类化合物及相关化合物脱氧的高效程序被提出。在甲酸存在下，它们的还原会导致它们的去羟基衍生物，而不影响其他功能团。
• Seboek Peter, Timar Tibor, Eszenyi Tibor, J. Org. Chem, 59 (1994) N 21, S 6318- 6321
  作者：Seboek Peter, Timar Tibor, Eszenyi Tibor

  DOI：——

  日期：——
• CAMPS, F.;COLL, J.;COLOMINA, O.;MESSEGUER, A., J. HETEROCYCL. CHEM., 1985, 22, N 2, 363-368
  作者：CAMPS, F.、COLL, J.、COLOMINA, O.、MESSEGUER, A.

  DOI：——

  日期：——
• Modification of Hydroxybenzopyranoids: Facile Deoxygenation of 2,2-Dimethyl-7-hydroxy-4-chromanones and a New Approach to Their Novel Mercapto Analogs
  作者：Peter Sebok、Tibor Timar、Tibor Eszenyi、Tamas Patonay

  DOI：10.1021/jo00100a038

  日期：1994.10

  A facile deoxygenation of a systematic series of substituted 2,2-dimethyl-7-hydroxy-4-chromanones via their sulfonate, isourea, and thiocarbamate derivatives is reported. The synthesis of novel 2,2-dimethyl-7-mercapto-4-chromanones has been accomplished by the hydrolysis of the corresponding thiocarbamates. The scope and limitations of different deoxygenation procedures in the case of these hydroxybenzopyranoids are also presented.