8-ethyl-1-methoxy-6H-benzonaphtho<1,2-b>pyran-6-one | 114862-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 8-ethyl-1-methoxy-6H-benzonaphtho<1,2-b>pyran-6-one
• 英文别名: 8-ethyl-1-methoxybenzonaphtho<1,2-b>pyran-6-one；8-Ethyl-1-methoxynaphtho[1,2-c]isochromen-6-one
• CAS: 114862-65-6
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: NPIDQRGSFKSXMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-ethyl-1-methoxy-6H-benzonaphtho<1,2-b>pyran-6-one 在 吡啶 、 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 18-冠醚-6 、 三溴化硼 、 四氯化锡 、 cesium fluoride 作用下， 以 四氯化碳 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.67h， 生成 [3-acetyloxy-5-[1-acetyloxy-8-(1-bromoethyl)-6-oxonaphtho[1,2-c]isochromen-4-yl]furan-2-yl]methyl acetate
  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：

  methyl 5-ethyl-2-oxo-cyclohexancarboxylate 在 palladium on activated charcoal 硫酸 、 potassium carbonate 作用下， 以 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 8-ethyl-1-methoxy-6H-benzonaphtho<1,2-b>pyran-6-one
  参考文献：
  名称：

  The photobiology of the gilvocarcins. Total synthesis of defucogilvocarcin V and a related photoactive vinyl phenol

  摘要：

  DOI：

  10.1021/jo00251a008

文献信息

• 8-Ethyl-1-methoxybenzo[d]naphtho[1,2-b]pyran-6-one C-glycosides by acid-catalyzed glycosylation
  作者：Daw Iong Kwok、Robert A. Outten、Robert Huhn、G. Doyle Daves

  DOI：10.1021/jo00257a032

  日期：1988.10
• KWOK, DAW-IONG;DAVES, G. DOYLE (JR), J. ORG. CHEM., 54,(1989) N9, C. 4496-4497
  作者：KWOK, DAW-IONG、DAVES, G. DOYLE (JR)

  DOI：——

  日期：——
• FARR, ROGER N.;OUTTEN, ROBERT A.;CHENG, JANE CHI-YA;DAVES, G. DOYLE (JR), ORGANOMETALLICS, 9,(1990) N2, C. 3151-3156
  作者：FARR, ROGER N.、OUTTEN, ROBERT A.、CHENG, JANE CHI-YA、DAVES, G. DOYLE (JR)

  DOI：——

  日期：——
• MCGEE, LAWRENCE R.;CONFALONE, PAT N., J. ORG. CHEM., 53,(1988) N 16, 3695-3701
  作者：MCGEE, LAWRENCE R.、CONFALONE, PAT N.

  DOI：——

  日期：——
• KWOK, DAW-IONG;OUTTEN, ROBERT A.;HUHN, ROBERT;DAVES, G. DOYLE (JR), J. ORG. CHEM., 53,(1988) N 22, C. 5359-5361
  作者：KWOK, DAW-IONG、OUTTEN, ROBERT A.、HUHN, ROBERT、DAVES, G. DOYLE (JR)

  DOI：——

  日期：——