5-methyl-1-(2,4,6-trimethoxymethoxyphenyl)hex-4-en-1-one | 625456-32-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methyl-1-(2,4,6-trimethoxymethoxyphenyl)hex-4-en-1-one
• 英文别名: 5-Methyl-1-[2,4,6-tris(methoxymethoxy)phenyl]hex-4-en-1-one
• CAS: 625456-32-8
• 化学式: C₁₉H₂₈O₇
• 分子量: 368.427
• InChiKey: JNXPZSZWLLWELH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methyl-1-(2,4,6-trimethoxymethoxyphenyl)hex-4-en-1-one 在 盐酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 30.5h， 生成 (2,3)-trans-3-(3'',3''-dimethylallyl)-5,7,2',4'-tetrahydroxyflavanone
  参考文献：
  名称：

  First Synthesis of (±)-C-3-Prenylated Flavanones

  摘要：

  2,4,6-tris(Methoxymethoxy)acetophenone (1) was first mono-alkylated with 3-methylbut-2-enyl bromide to yield 5-methyl-1-(2,4,6-trimethoxymethoxyphenyl)hex-4-en-1-one (2): The base catalyzed aldol condensation of 2 and substituted benzaldehydes gave chalcones 3 in good yields. One pot cyclization and deprotection of the chalcones were accomplished in refluxing 4N HCl inMeOH to afford (+/-)-C-3-prenylated flavanones.

  DOI：

  10.1081/scc-120021998
• 作为产物：
  描述：

  1-[2,4,6-三(甲氧基甲氧基)苯基]乙酮 、 1-溴-3-甲基-2-丁烯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.5h， 以50%的产率得到5-methyl-1-(2,4,6-trimethoxymethoxyphenyl)hex-4-en-1-one
  参考文献：
  名称：

  First Synthesis of (±)-C-3-Prenylated Flavanones

  摘要：

  2,4,6-tris(Methoxymethoxy)acetophenone (1) was first mono-alkylated with 3-methylbut-2-enyl bromide to yield 5-methyl-1-(2,4,6-trimethoxymethoxyphenyl)hex-4-en-1-one (2): The base catalyzed aldol condensation of 2 and substituted benzaldehydes gave chalcones 3 in good yields. One pot cyclization and deprotection of the chalcones were accomplished in refluxing 4N HCl inMeOH to afford (+/-)-C-3-prenylated flavanones.

  DOI：

  10.1081/scc-120021998

文献信息

• First Synthesis of (±)-<i>C</i>-3-Prenylated Flavanones
  作者：Jin Xu、Haishan Wang、Mui Mui Sim

  DOI：10.1081/scc-120021998

  日期：2003.1.8

  2,4,6-tris(Methoxymethoxy)acetophenone (1) was first mono-alkylated with 3-methylbut-2-enyl bromide to yield 5-methyl-1-(2,4,6-trimethoxymethoxyphenyl)hex-4-en-1-one (2): The base catalyzed aldol condensation of 2 and substituted benzaldehydes gave chalcones 3 in good yields. One pot cyclization and deprotection of the chalcones were accomplished in refluxing 4N HCl inMeOH to afford (+/-)-C-3-prenylated flavanones.