4-(3-hydroxyprop-1-yn-1-yl)-2-methoxyphenol | 1486420-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(3-hydroxyprop-1-yn-1-yl)-2-methoxyphenol
• 英文别名: 4-(3-Hydroxyprop-1-ynyl)-2-methoxyphenol；4-(3-hydroxyprop-1-ynyl)-2-methoxyphenol
• CAS: 1486420-55-6
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: BPIXCQXVCXQUPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxyprop-1-yn-1-yl)-2-methoxyphenol 在 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以51%的产率得到(Z)-4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenol
  参考文献：
  名称：

  Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle

  摘要：

  The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin's catechol moiety, and finally, further oxidation to form four of the major components of silymarin: silybin A, silybin B, isosilybin A, and isosilybin B. This mechanism is significantly different from a previously proposed process that involves the coupling of two independently formed radicals.

  DOI：

  10.1021/jo4011377
• 作为产物：
  描述：

  4-溴邻甲氧基苯酚 、 2-丙炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 4.0h， 以9%的产率得到4-(3-hydroxyprop-1-yn-1-yl)-2-methoxyphenol
  参考文献：
  名称：

  Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle

  摘要：

  The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin's catechol moiety, and finally, further oxidation to form four of the major components of silymarin: silybin A, silybin B, isosilybin A, and isosilybin B. This mechanism is significantly different from a previously proposed process that involves the coupling of two independently formed radicals.

  DOI：

  10.1021/jo4011377

文献信息

• Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle
  作者：Hanan S. Althagafy、Maria Elena Meza-Aviña、Nicholas H. Oberlies、Mitchell P. Croatt

  DOI：10.1021/jo4011377

  日期：2013.8.2

  The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin's catechol moiety, and finally, further oxidation to form four of the major components of silymarin: silybin A, silybin B, isosilybin A, and isosilybin B. This mechanism is significantly different from a previously proposed process that involves the coupling of two independently formed radicals.