2-[(tert-Butyl-dimethyl-silanyloxy)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-3-[(3,4-dimethoxy-phenyl)-hydroxy-methyl]-succinic acid dimethyl ester | 165257-95-4

• 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: 2-[(tert-Butyl-dimethyl-silanyloxy)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-3-[(3,4-dimethoxy-phenyl)-hydroxy-methyl]-succinic acid dimethyl ester
• CAS: 165257-95-4
• 化学式: C₃₂H₄₅NO₁₁Si
• 分子量: 647.795
• InChiKey: JASLGUHZCSQFCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  45.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  152.0
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-[(tert-Butyl-dimethyl-silanyloxy)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-3-[(3,4-dimethoxy-phenyl)-hydroxy-methyl]-succinic acid dimethyl ester 在 三氟乙酸 作用下， 以7%的产率得到4-[(tert-Butyl-dimethyl-silanyloxy)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-2-(3,4-dimethoxy-phenyl)-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester
  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：

  α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4,5-trimethoxyphenyl)acetonitrile 、 马来酸二甲酯 、 3,4-二甲氧基苯甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以78%的产率得到2-[(tert-Butyl-dimethyl-silanyloxy)-cyano-(3,4,5-trimethoxy-phenyl)-methyl]-3-[(3,4-dimethoxy-phenyl)-hydroxy-methyl]-succinic acid dimethyl ester
  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