(+/-)-6-(4'-methoxyphenylmethoxy)-1,2-hexadien-4-ol | 154366-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-6-(4'-methoxyphenylmethoxy)-1,2-hexadien-4-ol
• 英文别名: 1-[(4-methoxyphenyl)methoxy]hexa-4,5-dien-3-ol
• CAS: 154366-13-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: XSTQFQLFZCZGSR-UHFFFAOYSA-N

物化性质

• 沸点：
  383.4±21.0 °C(predicted)
• 密度：
  1.033±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-6-(4'-methoxyphenylmethoxy)-1,2-hexadien-4-ol 在 2,6-二甲基吡啶 、 pH 7 buffer 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (+/-)-3-(t-butyldimethylsilyloxy)-4,5-hexadien-1-ol
  参考文献：
  名称：

  Furanosides and furanones bearing acrylate sidechains via palladium-mediated cyclizations of γ-Oxoallenes

  摘要：

  Treatment of 4,5-hexadienal with catalytic palladium(II) chloride and excess copper(II) chloride, methanol and carbon monoxide in the presence of an acid and a water scavenger resulted in a net acetalization-cyclization-methoxycarbonylation to form a novel methyl furanoside bearing a methyl acrylate sidechain. Treatment of 4,5-hexadienoic acid under the same conditions yields the corresponding furanone, and 3-(tert-butylidimethylsilyloxy)-4,5-hexadienal yields a methyl beta-3'-(tert-butyldimethylsilyloxy)-2'-deoxyribofuranoside bearing the acrylate sidechain, with high stereoselectivity. This methodology provides access to sidechain-branched ribofuranoside compounds.

  DOI：

  10.1016/0040-4020(93)80015-l
• 作为产物：
  描述：

  3-[(4-甲氧基苄基)氧基]-1-丙醇 在 lithium aluminium tetrahydride 、 正丁基锂 、 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (+/-)-6-(4'-methoxyphenylmethoxy)-1,2-hexadien-4-ol
  参考文献：
  名称：

  Furanosides and furanones bearing acrylate sidechains via palladium-mediated cyclizations of γ-Oxoallenes

  摘要：

  Treatment of 4,5-hexadienal with catalytic palladium(II) chloride and excess copper(II) chloride, methanol and carbon monoxide in the presence of an acid and a water scavenger resulted in a net acetalization-cyclization-methoxycarbonylation to form a novel methyl furanoside bearing a methyl acrylate sidechain. Treatment of 4,5-hexadienoic acid under the same conditions yields the corresponding furanone, and 3-(tert-butylidimethylsilyloxy)-4,5-hexadienal yields a methyl beta-3'-(tert-butyldimethylsilyloxy)-2'-deoxyribofuranoside bearing the acrylate sidechain, with high stereoselectivity. This methodology provides access to sidechain-branched ribofuranoside compounds.

  DOI：

  10.1016/0040-4020(93)80015-l

文献信息

• Furanosides and furanones bearing acrylate sidechains via palladium-mediated cyclizations of γ-Oxoallenes
  作者：Robert D. Walkup、Michael D. Mosher

  DOI：10.1016/0040-4020(93)80015-l

  日期：1993.1

  Treatment of 4,5-hexadienal with catalytic palladium(II) chloride and excess copper(II) chloride, methanol and carbon monoxide in the presence of an acid and a water scavenger resulted in a net acetalization-cyclization-methoxycarbonylation to form a novel methyl furanoside bearing a methyl acrylate sidechain. Treatment of 4,5-hexadienoic acid under the same conditions yields the corresponding furanone, and 3-(tert-butylidimethylsilyloxy)-4,5-hexadienal yields a methyl beta-3'-(tert-butyldimethylsilyloxy)-2'-deoxyribofuranoside bearing the acrylate sidechain, with high stereoselectivity. This methodology provides access to sidechain-branched ribofuranoside compounds.