(2RS)-3,4-Dihydro-2-(hydroxymethyl)-2-methyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one | 104250-10-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (2RS)-3,4-Dihydro-2-(hydroxymethyl)-2-methyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one
• 英文别名: 2-(hydroxymethyl)-2-methyl-3,4-dihydro-2H,5H-pyrano<3,2-c><1>benzopyran-5-one；2-methyl-3,4-dihydro-2-hydroxymethyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one；2-methyl-2-hydroxymethylpyrano<3,2-c><1>benzopyran-5-one；2-methyl-2-hydroxymethylpyrano[3,2-c][1]benzopyran-5-one；2-(Hydroxymethyl)-2-methyl-3,4-dihydropyrano[3,2-c]chromen-5-one
• CAS: 104250-10-4
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: MGGCJHKMPYYLPX-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  438.3±40.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS)-3,4-Dihydro-2-(hydroxymethyl)-2-methyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one 在 sodium methylate 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 (3'RS)-(4'Z)-Isoferprenin
  参考文献：
  名称：

  The Chemistry of Coumarin Derivatives. Part VI. Diels-Alder Trapping of 3-Methylene-2,4-chromandione. A New Entry to Substituted Pyrano[3,2-c]coumarins

  摘要：

  3-Methylene-2,4-chromandione (1) can be generated from dicumarol or from paraformaldehyde and 4-hydroxycoumarin. 1 is a versatile substrate for cycloaddition reactions. Depending on the reaction partner, 1 can behave as an ambident heterodiene or as a dienophile. The reaction was investigated with a series of olefins and dienes, including several isoprenoids. Some generalizations could be drawn and rationalized in terms of HOMO-LUMO interactions. The reaction of 1 and certain asymmetrically substituted olefins gives pyrano[3,2-c]coumarins in a highly regio- and chemoselective way. As an application of this reaction to natural products chemistry, a concise (three steps) synthesis of the prenylated coumarin (+/-)-isoferprenin (35a) is reported.

  DOI：

  10.1021/jo00098a013
• 作为产物：
  描述：

  2-(chloromercurymethyl)-2-methyl-3,4-dihydro-2H,5H-pyrano<3,2-c><1>benzopyran-5-one 在 tetrabutylammonium borohydride 作用下， 以 甲醇 、 四氯化碳 、 水 为溶剂， 以42.5%的产率得到2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  Bravo, Pierfrancesco; Ticozzi, Calimero; Viani, Fiorenza, Gazzetta Chimica Italiana, 1985, vol. 115, # 12, p. 677 - 684

  摘要：

  DOI：

文献信息

• Bravo, Pierfrancesco; Resnati, Giuseppe; Ticozzi, Calimero, Gazzetta Chimica Italiana, 1986, vol. 116, # 9, p. 491 - 500
  作者：Bravo, Pierfrancesco、Resnati, Giuseppe、Ticozzi, Calimero、Arnone, Alberto、Cavicchio, Giancarlo

  DOI：——

  日期：——
• Bravo, Pierfrancesco; Resnati, Giuseppe; Ticozzi, Calimero, Gazzetta Chimica Italiana, 1986, vol. 116, # 9, p. 501 - 510
  作者：Bravo, Pierfrancesco、Resnati, Giuseppe、Ticozzi, Calimero、Arnone, Alberto、Cavicchio, Giancarlo

  DOI：——

  日期：——
• Bravo, Pierfrancesco; Ticozzi, Calimero; Arnone, Alberto, Gazzetta Chimica Italiana, 1987, vol. 117, # 9, p. 539 - 548
  作者：Bravo, Pierfrancesco、Ticozzi, Calimero、Arnone, Alberto、Ganazzoli, Fabio、Cavicchio, Giancarlo、Albinati, Alberto

  DOI：——

  日期：——
• BRAVO, P.;TICOZZI, C.;VIANI, F.;ARNONE, A., GAZZ. CHIM. ITAL., 1985, 115, N 12, 677-684
  作者：BRAVO, P.、TICOZZI, C.、VIANI, F.、ARNONE, A.

  DOI：——

  日期：——
• BRAVO P.; RESNATI G.; TICOZZI C.; ARNONE A.; CAVICCHIO G., GAZZ. CHIM. ITAL., 116,(1986) N 9, 491-499
  作者：BRAVO P.、 RESNATI G.、 TICOZZI C.、 ARNONE A.、 CAVICCHIO G.

  DOI：——

  日期：——