8-ethyl-4-iodo-1-(trimethylacetoxy)benzonaphtho<1,2-b>pyran-6-one | 139277-27-3

• 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: 8-ethyl-4-iodo-1-(trimethylacetoxy)benzonaphtho<1,2-b>pyran-6-one
• 英文别名: (8-Ethyl-4-iodo-6-oxonaphtho[1,2-c]isochromen-1-yl) 2,2-dimethylpropanoate
• CAS: 139277-27-3
• 化学式: C₂₄H₂₁IO₄
• 分子量: 500.333
• InChiKey: LCCCWOPAZOZSGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-ethyl-4-iodo-1-(trimethylacetoxy)benzonaphtho<1,2-b>pyran-6-one 在 palladium diacetate 、 三正丁胺 、 四丁基氟化铵 、 sodium acetate 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 2,2-Dimethyl-propionic acid 8-ethyl-4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester
  参考文献：
  名称：

  8-Ethenyl-1-hydroxy-4-.beta.-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one and 8-ethenyl-1-hydroxy-4-(2'-deoxy-.beta.-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one. Synthetic C-glycosides related to the gilvocarcin, ravidomycin, and chrysomycin antibiotics

  摘要：

  Syntheses of 8-ethenyl-1-hydroxy-4-beta-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one (1) and 8-ethenyl-1-hydroxy-4-(2'-deoxy-beta-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one (2) have been accomplished. These two compounds are the first synthetic C-glycosides structurally related to the gilvocarcin, ravidomycin, and chrysomycin antibiotic class which possess the aglycon substituents (hydroxyl at C-1 and ethenyl at C-8) considered critical for the photolytic nicking of DNA. Anthracycline C-glycoside 1 was prepared by a route involving Lewis acid-catalyzed C-glycosyl bond formation between the tetracyclic aglycon and 1,2,3,5-tetra-O-acetyl-D-ribose followed by construction of the aglycon 8-ethenyl substituent from the corresponding ethyl group by radical bromination-dehydrobromination. Synthesis of C-glycoside 2 utilized a different, complementary procedure for C-glycosyl bond formation by palladium-mediated coupling of an iodoaglycon derivative with 1,4-anhydro-2-deoxy-3-O-(tert-butyldiphenylsilyl)-D-erythro-pent-1-enitol, a furanoid glycal designed to form only beta-C-glycosyl bonds in this reaction. In the synthesis of 2, the 8-ethenyl substituent of the aglycon was installed prior to C-glycosyl bond formation since, in this case, attempted ethyl group bromination led instead to conversion of the carbohydrate moiety to a furan.

  DOI：

  10.1021/jo00033a034
• 作为产物：
  描述：

  4-bromo-8-ethyl-1-methoxybenzonaphtho<1,2-b>pyran-6-one 在 4-二甲氨基吡啶 、 copper(l) iodide 、 三溴化硼 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 8-ethyl-4-iodo-1-(trimethylacetoxy)benzonaphtho<1,2-b>pyran-6-one
  参考文献：
  名称：

  8-Ethenyl-1-hydroxy-4-.beta.-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one and 8-ethenyl-1-hydroxy-4-(2'-deoxy-.beta.-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one. Synthetic C-glycosides related to the gilvocarcin, ravidomycin, and chrysomycin antibiotics

  摘要：

  Syntheses of 8-ethenyl-1-hydroxy-4-beta-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one (1) and 8-ethenyl-1-hydroxy-4-(2'-deoxy-beta-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one (2) have been accomplished. These two compounds are the first synthetic C-glycosides structurally related to the gilvocarcin, ravidomycin, and chrysomycin antibiotic class which possess the aglycon substituents (hydroxyl at C-1 and ethenyl at C-8) considered critical for the photolytic nicking of DNA. Anthracycline C-glycoside 1 was prepared by a route involving Lewis acid-catalyzed C-glycosyl bond formation between the tetracyclic aglycon and 1,2,3,5-tetra-O-acetyl-D-ribose followed by construction of the aglycon 8-ethenyl substituent from the corresponding ethyl group by radical bromination-dehydrobromination. Synthesis of C-glycoside 2 utilized a different, complementary procedure for C-glycosyl bond formation by palladium-mediated coupling of an iodoaglycon derivative with 1,4-anhydro-2-deoxy-3-O-(tert-butyldiphenylsilyl)-D-erythro-pent-1-enitol, a furanoid glycal designed to form only beta-C-glycosyl bonds in this reaction. In the synthesis of 2, the 8-ethenyl substituent of the aglycon was installed prior to C-glycosyl bond formation since, in this case, attempted ethyl group bromination led instead to conversion of the carbohydrate moiety to a furan.

  DOI：

  10.1021/jo00033a034