2,4-O-benzylidene-3,5-O-dibenzoyl-D-ribose | 83162-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-O-benzylidene-3,5-O-dibenzoyl-D-ribose
• CAS: 83162-62-3；89300-72-1
• 化学式: C₂₆H₂₂O₇
• 分子量: 446.456
• InChiKey: QQDYYRVYAXDVQL-LNEBKTTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4-O-benzylidene-3,5-O-dibenzoyl-D-ribose 在 吡啶 、 盐酸 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 为溶剂， 反应 120.0h， 生成 3-(3',5'-O-dibenzoyl-D-ribosylidene)-2,4-pentanedione
  参考文献：
  名称：

  Antiviral compounds. 1. Structure-activity relationship of some antiviral enediones derived from aldehydo sugars

  摘要：

  A series of aldehydo sugars was subjected to condensation reactions with active methylene compounds. Acetylacetone was condensed with 2,4-O-benzylidene-3,5-O-dibenzoyl-D-ribose (1), 2,4:3,5-O-dibenzylidene-D-ribose (6), 2,3,4,5-tetraacetyl-D-ribose (7), and 2,3,4,5,6-pentaacetyl-D-glucose (9) to yield 3-ylidene-2,4-pentanedione derivatives 2, 11, 12, and 13, respectively. Sugar derivatives 1 and 6 were also condensed with benzoylacetone to give 14 and 18, with acetoacetanilide to give 16 and 19, with malononitrile to give 17 and 20, and with alpha-(gamma-butyrolactonylidene)triphenylphosphorane to give 21 and 22, respectively. Condensation of 1 with dibenzoylmethane gave 15. The double bond in compounds 2 and 11 was saturated by hydrogenation to give 23 and 24. All alpha, beta-unsaturated carbonyl compounds obtained exhibited antiviral activity and cytotoxicity. Compound 11 was found to have the most significant and selective antiviral activity against herpes simplex virus.

  DOI：

  10.1021/jm00355a007