(7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetic acid 2-[(2S,3S,3aR,6aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-hexahydro-furo[2,3-b]furan-3-yl]-ethyl ester | 885218-45-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetic acid 2-[(2S,3S,3aR,6aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-hexahydro-furo[2,3-b]furan-3-yl]-ethyl ester
• CAS: 885218-45-1
• 化学式: C₃₈H₄₃NO₈Si
• 分子量: 669.847
• InChiKey: SGMMOYLHJRLGJH-NPCLSRNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  48.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  104.51
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetic acid 2-[(2S,3S,3aR,6aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-hexahydro-furo[2,3-b]furan-3-yl]-ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到2-[(2S,3S,3aR,6aR)-2-(hydroxymethyl)-5-oxo-3,3a,4,6a-tetrahydro-2H-furo[2,3-b]furan-3-yl]ethyl 2-[7-(dimethylamino)-2-oxochromen-4-yl]acetate
  参考文献：
  名称：

  Chemical Analysis of Norrisolide-Induced Golgi Vesiculation

  摘要：

  The chemical origin of the norrisolide-induced irreversible Golgi vesiculation was studied using a variety of norrisolide probes. This natural product was found to bind to a receptor on the Golgi membranes using the perhydroindane core fragment as the recognition element. The acetylated gamma-lactol-gamma-lactone side chain of norrisolide is essential for the irreversible Golgi vesiculation and can be replaced by other electrophilic motifs without loss of biological function. In particular, compound 10 reproduces the cellular phenotype of the natural product.

  DOI：

  10.1021/ja058259a
• 作为产物：
  描述：

  2-[(3aR,4S,5S,6aR)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl]acetaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 4 A molecular sieve 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.17h， 生成 (7-Dimethylamino-2-oxo-2H-chromen-4-yl)-acetic acid 2-[(2S,3S,3aR,6aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-hexahydro-furo[2,3-b]furan-3-yl]-ethyl ester
  参考文献：
  名称：

  Chemical Analysis of Norrisolide-Induced Golgi Vesiculation

  摘要：

  The chemical origin of the norrisolide-induced irreversible Golgi vesiculation was studied using a variety of norrisolide probes. This natural product was found to bind to a receptor on the Golgi membranes using the perhydroindane core fragment as the recognition element. The acetylated gamma-lactol-gamma-lactone side chain of norrisolide is essential for the irreversible Golgi vesiculation and can be replaced by other electrophilic motifs without loss of biological function. In particular, compound 10 reproduces the cellular phenotype of the natural product.

  DOI：

  10.1021/ja058259a