3,4-dihydro-1-methoxy-3-phenyl-1H-2-benzopyran-3-yl hydroperoxide | 145430-77-9

• 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: 3,4-dihydro-1-methoxy-3-phenyl-1H-2-benzopyran-3-yl hydroperoxide
• 英文别名: 3-Hydroperoxy-1-methoxy-3-phenyl-1,4-dihydroisochromene
• CAS: 145430-77-9
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: AJFYNHTXFVODSL-UHFFFAOYSA-N

物化性质

• 沸点：
  430.9±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-1-methoxy-3-phenyl-1H-2-benzopyran-3-yl hydroperoxide 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以75%的产率得到1-methoxy-3-phenyl-1H-isochromene
  参考文献：
  名称：

  Ozonolyses of 1,2-diphenyl- and 2-phenylindene

  摘要：

  Ozonolyses of 1,2-diphenylindene (7), 2-phenylindene (18), and the structurally related acyclic keto olefins 13, 14, 26, and 32 were conducted in MeOH/CH2Cl2 at -70 and 0-degrees-C. The structure of the indenes, 7 and 18, and the reaction temperature, were found to exert an influence on the outcome of the reaction. Ozonolysis of 1,2-diphenylindene (7) at -70-degrees-C proceeded exclusively via the carbonyl oxide intermediate 15 providing the methanol-derived isochroman 9a as the sole isolable product. In contrast, four methanol-derived products, 20-23, were obtained from 2-phenylindene (18) under similar reaction conditions, suggesting that the primary ozonide 25 from 18 undergoes two competing modes of decomposition. Ozonolyses of indenes, 7 and 18, and 0-degrees-C gave mainly the corresponding ozonides, 8 and 19, respectively, while analogous reactions at -70-degrees-C resulted in the predominant formation of the methanol-derived products 9 and 20-23, respectively. The major differences in composition between the ozonolysis product mixtures derived from the acyclic keto olefins 13, 14, 26, and 32 and the appropriate corresponding indenes 7 and 18 suggest that the intermediate carbonyl oxides generated from the former do not make significant contributions to the reaction pathways of the latter.

  DOI：

  10.1021/jo00053a026
• 作为产物：
  描述：

  2-苯基茚 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以19%的产率得到3,4-dihydro-1-methoxy-3-phenyl-1H-2-benzopyran-3-yl hydroperoxide
  参考文献：
  名称：

  Ozonolyses of 1,2-diphenyl- and 2-phenylindene

  摘要：

  Ozonolyses of 1,2-diphenylindene (7), 2-phenylindene (18), and the structurally related acyclic keto olefins 13, 14, 26, and 32 were conducted in MeOH/CH2Cl2 at -70 and 0-degrees-C. The structure of the indenes, 7 and 18, and the reaction temperature, were found to exert an influence on the outcome of the reaction. Ozonolysis of 1,2-diphenylindene (7) at -70-degrees-C proceeded exclusively via the carbonyl oxide intermediate 15 providing the methanol-derived isochroman 9a as the sole isolable product. In contrast, four methanol-derived products, 20-23, were obtained from 2-phenylindene (18) under similar reaction conditions, suggesting that the primary ozonide 25 from 18 undergoes two competing modes of decomposition. Ozonolyses of indenes, 7 and 18, and 0-degrees-C gave mainly the corresponding ozonides, 8 and 19, respectively, while analogous reactions at -70-degrees-C resulted in the predominant formation of the methanol-derived products 9 and 20-23, respectively. The major differences in composition between the ozonolysis product mixtures derived from the acyclic keto olefins 13, 14, 26, and 32 and the appropriate corresponding indenes 7 and 18 suggest that the intermediate carbonyl oxides generated from the former do not make significant contributions to the reaction pathways of the latter.

  DOI：

  10.1021/jo00053a026

文献信息

• Ozonolyses of 1,2-diphenyl- and 2-phenylindene
  作者：Toshiya Sugimoto、Koichi Teshima、Norinaga Nakamura、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/jo00053a026

  日期：1993.1

  Ozonolyses of 1,2-diphenylindene (7), 2-phenylindene (18), and the structurally related acyclic keto olefins 13, 14, 26, and 32 were conducted in MeOH/CH2Cl2 at -70 and 0-degrees-C. The structure of the indenes, 7 and 18, and the reaction temperature, were found to exert an influence on the outcome of the reaction. Ozonolysis of 1,2-diphenylindene (7) at -70-degrees-C proceeded exclusively via the carbonyl oxide intermediate 15 providing the methanol-derived isochroman 9a as the sole isolable product. In contrast, four methanol-derived products, 20-23, were obtained from 2-phenylindene (18) under similar reaction conditions, suggesting that the primary ozonide 25 from 18 undergoes two competing modes of decomposition. Ozonolyses of indenes, 7 and 18, and 0-degrees-C gave mainly the corresponding ozonides, 8 and 19, respectively, while analogous reactions at -70-degrees-C resulted in the predominant formation of the methanol-derived products 9 and 20-23, respectively. The major differences in composition between the ozonolysis product mixtures derived from the acyclic keto olefins 13, 14, 26, and 32 and the appropriate corresponding indenes 7 and 18 suggest that the intermediate carbonyl oxides generated from the former do not make significant contributions to the reaction pathways of the latter.