3-Methyl-3-carbaethoxy-5,6-benzo-3,4-dihydro-cumarin | 109733-90-6

• 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: 3-Methyl-3-carbaethoxy-5,6-benzo-3,4-dihydro-cumarin
• 英文别名: 2-methyl-3-oxo-2,3-dihydro-1H-benzo[f]chromene-2-carboxylic acid ethyl ester
• CAS: 109733-90-6
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: KBPPDTMPARUDTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Methyl-3-carbaethoxy-5,6-benzo-3,4-dihydro-cumarin 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-Hydroxy-naphthalen-1-ylmethyl)-2-methyl-malonic acid
  参考文献：
  名称：

  Inhibitors of Sir2:  Evaluation of Splitomicin Analogues

  摘要：

  Splitomicin (1) and 41 analogues were prepared and evaluated in cell-based Sir2 inhibition and toxicity assays and an in vitro Sir2 inhibition assay. Lactone ring or naphthalene (positions 7-9) substituents decrease activity, but other naphthalene substitutions (positions 5 and 6) are well-tolerated. The hydrolytically unstable aromatic lactone is important for activity. Lactone hydrolysis rates were used as a measure of reactivity; hydrolysis rates correlate with inhibitory activity. The most potent Sir2 inhibitors were structurally similar to and had hydrolysis rates similar to 1.

  DOI：

  10.1021/jm030473r
• 作为产物：
  描述：

  2-羟基-1-萘甲醛 在 哌啶 、 吡啶 、 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙基苯 为溶剂， 反应 17.0h， 生成 3-Methyl-3-carbaethoxy-5,6-benzo-3,4-dihydro-cumarin
  参考文献：
  名称：

  Inhibitors of Sir2:  Evaluation of Splitomicin Analogues

  摘要：

  Splitomicin (1) and 41 analogues were prepared and evaluated in cell-based Sir2 inhibition and toxicity assays and an in vitro Sir2 inhibition assay. Lactone ring or naphthalene (positions 7-9) substituents decrease activity, but other naphthalene substitutions (positions 5 and 6) are well-tolerated. The hydrolytically unstable aromatic lactone is important for activity. Lactone hydrolysis rates were used as a measure of reactivity; hydrolysis rates correlate with inhibitory activity. The most potent Sir2 inhibitors were structurally similar to and had hydrolysis rates similar to 1.

  DOI：

  10.1021/jm030473r