methyl 5-methoxy-2-(methoxymethyloxy)benzoate | 51985-42-3

• 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: methyl 5-methoxy-2-(methoxymethyloxy)benzoate
• 英文别名: Methyl 5-methoxy-2-(methoxymethoxy)benzoate
• CAS: 51985-42-3
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: JGALNNQENQQYQP-UHFFFAOYSA-N

物化性质

• 沸点：
  333.0±32.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-methoxy-2-(methoxymethyloxy)benzoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以9.0 g的产率得到(5-methoxy-2-(methoxymethoxy)phenyl)-methan-1-ol
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Riccardiphenols A and B, Isolated from the Liverwort Riccardia crassa

  摘要：

  The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.

  DOI：

  10.1021/jo952253u
• 作为产物：
  描述：

  2,5-二羟基苯甲酸甲酯 在 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 7.0h， 生成 methyl 5-methoxy-2-(methoxymethyloxy)benzoate
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Riccardiphenols A and B, Isolated from the Liverwort Riccardia crassa

  摘要：

  The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.

  DOI：

  10.1021/jo952253u

文献信息

• Synthesis and Structure−Activity Relationship Study of Lamellarin Derivatives
  作者：Fumito Ishibashi、Shinji Tanabe、Tatsuya Oda、Masatomo Iwao

  DOI：10.1021/np0104525

  日期：2002.4.1

  Ten derivatives (3-12) of marine alkaloid lamellarin D (1) were synthesized and evaluated for cytotoxicity against a HeLa cell line in an effort to examine their structure-activity relationships. It appeared that the hydroxyl groups at positions C-8 and C-20 of 1 were important structural requirements for cytotoxic activity, while the hydroxyl group at C-14 and the two methoxy groups at C-13 and C-21 were not necessary for the activity.
• Total Synthesis and Absolute Configuration of Riccardiphenols A and B, Isolated from the Liverwort <i>Riccardia crassa</i>
  作者：Motoo Tori、Tomonobu Hamaguchi、Kumiko Sagawa、Masakazu Sono、Yoshinori Asakawa

  DOI：10.1021/jo952253u

  日期：1996.1.1

  The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.