Methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)benzo[f][1,3]benzodioxole-6-carboxylate | 7404-90-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: Methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)benzo[f][1,3]benzodioxole-6-carboxylate
• CAS: 7404-90-2
• 化学式: C₂₃H₂₂O₉
• 分子量: 442.422
• InChiKey: JNTLCPHNRUMXLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)benzo[f][1,3]benzodioxole-6-carboxylate 在 盐酸 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 四去氢鬼臼毒素
  参考文献：
  名称：

  Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins

  摘要：

  1-Arylnaphthalene lignan lactones were synthesized in good yields from O-(tert-butyldimethylsilyl)cyanohydrins in two steps based on a conjugate addition-aldol reaction, followed by acid-catalyzed closure to form the naphthalene ring. 4-Hydroxy-1-arylnaphthalene lignan lactones were also synthesized by conjugate addition-aldol reaction, followed by aromatization-lactonization.

  DOI：

  10.1021/jo00119a041
• 作为产物：
  描述：

  (5S,6R)-7-[1-Hydroxy-meth-(E)-ylidene]-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 在 sodium methylate 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 Methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)benzo[f][1,3]benzodioxole-6-carboxylate
  参考文献：
  名称：

  Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins

  摘要：

  1-Arylnaphthalene lignan lactones were synthesized in good yields from O-(tert-butyldimethylsilyl)cyanohydrins in two steps based on a conjugate addition-aldol reaction, followed by acid-catalyzed closure to form the naphthalene ring. 4-Hydroxy-1-arylnaphthalene lignan lactones were also synthesized by conjugate addition-aldol reaction, followed by aromatization-lactonization.

  DOI：

  10.1021/jo00119a041

文献信息

• Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins
  作者：Tsuyoshi Ogiku、Sin-ich Yoshida、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo00119a041

  日期：1995.7

  1-Arylnaphthalene lignan lactones were synthesized in good yields from O-(tert-butyldimethylsilyl)cyanohydrins in two steps based on a conjugate addition-aldol reaction, followed by acid-catalyzed closure to form the naphthalene ring. 4-Hydroxy-1-arylnaphthalene lignan lactones were also synthesized by conjugate addition-aldol reaction, followed by aromatization-lactonization.