Methyl 5-methoxy-2-(methoxymethoxy)-4-phenylmethoxybenzoate | 190278-33-2

• 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-(methoxymethoxy)-4-phenylmethoxybenzoate
• CAS: 190278-33-2
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: YTDJVYKAFWZNAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 5-methoxy-2-(methoxymethoxy)-4-phenylmethoxybenzoate 在 盐酸 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 26.5h， 生成 3,11-bis(benzyloxy)-2,12-dimethoxy-14-(3-methoxyphenyl)-6H[1]benzopyrano[4',3':4,5]pyrrolo[2,1-a]isoquinoline-6-one
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Study of Lamellarin Derivatives

  摘要：

  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.

  DOI：

  10.1021/np0104525
• 作为产物：
  描述：

  4-benzyloxy-5-bromo-2-hydroxy-benzoic acid methyl ester 在 potassium tert-butylate 、 sodium 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 Methyl 5-methoxy-2-(methoxymethoxy)-4-phenylmethoxybenzoate
  参考文献：
  名称：

  Total Syntheses of Lamellarin D and H. The First Synthesis of Lamellarin-Class Marine Alkaloids

  摘要：

  Total syntheses of marine polyaromatic alkaloids, lamellarin D (1) and H (2), are described. The pentacyclic lamellarin ring system was constructed by B-ylide mediated pyrrole ring formation and subsequent lactonization of 4 obtained by an assembly of known benzylisoquinoline 5, benzoate 6 and ethyl bromoacetate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00287-1

文献信息

• Total Syntheses of Lamellarin D and H. The First Synthesis of Lamellarin-Class Marine Alkaloids
  作者：Fumito Ishibashi、Yuka Miyazaki、Masatomo Iwao

  DOI：10.1016/s0040-4020(97)00287-1

  日期：1997.4

  Total syntheses of marine polyaromatic alkaloids, lamellarin D (1) and H (2), are described. The pentacyclic lamellarin ring system was constructed by B-ylide mediated pyrrole ring formation and subsequent lactonization of 4 obtained by an assembly of known benzylisoquinoline 5, benzoate 6 and ethyl bromoacetate. (C) 1997 Elsevier Science Ltd.
• 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.