4-(benzo[d][1,3]dioxol-5-yl)-3-(2-fluorobenzoyl)-7,7-dimethyl-2-(phenylamino)-7,8-dihydro-4H-chromen-5(6H)-one | 1258214-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(benzo[d][1,3]dioxol-5-yl)-3-(2-fluorobenzoyl)-7,7-dimethyl-2-(phenylamino)-7,8-dihydro-4H-chromen-5(6H)-one
• 英文别名: 2-anilino-4-(1,3-benzodioxol-5-yl)-3-(2-fluorobenzoyl)-7,7-dimethyl-6,8-dihydro-4H-chromen-5-one
• CAS: 1258214-99-1
• 化学式: C₃₁H₂₆FNO₅
• 分子量: 511.55
• InChiKey: YTSQSCDHVMMWEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(benzo[d][1,3]dioxol-5-yl)-3-(2-fluorobenzoyl)-7,7-dimethyl-2-(phenylamino)-7,8-dihydro-4H-chromen-5(6H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以83%的产率得到12-(benzo[d][1,3]dioxol-5-yl)-3,3-dimethyl-6-phenyl-3,4,6,12-tetrahydro-1H-chromeno[2,3-b]quinoline-1,11(2H)-dione
  参考文献：
  名称：

  Reactivity of Functionalized N,S-Ketene Acetal: Regioselective Construction of Tetrahydrobenzo[b]pyran and Chromeno[2,3-b]quinoline Derivatives

  摘要：

  Regioselective synthesis of functionalized tetrahydrobenzo[b]pyrans has been developed by multi-component reactions (MCRs) and tandem [3 + 3] annulations of beta-benzoylthioacetanilides or beta-(2-haloaroyl)thioacetanilides as valuable sources with aromatic aldehydes and 5,5-dimethy1-1,3-cyclohexanedione catalyzed by triethylamine. This MCR followed by a postcondensation cyclization via an intramolecular SNAr in the presence of K2CO3 led to an unprecedented novel chromeno-[2,3-b]quinoline framework containing an important chromene moiety in good yields. The reactions were very mild, convenient, and o-selective to form new fused tetracyclic target molecules.

  DOI：

  10.1021/jo101902z
• 作为产物：
  描述：

  胡椒醛 、 3-(2-fluorophenyl)-3-oxo-N-phenylpropanethioamide 、 5,5-二甲基-1,3-环己二酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以44%的产率得到4-(benzo[d][1,3]dioxol-5-yl)-3-(2-fluorobenzoyl)-7,7-dimethyl-2-(phenylamino)-7,8-dihydro-4H-chromen-5(6H)-one
  参考文献：
  名称：

  Reactivity of Functionalized N,S-Ketene Acetal: Regioselective Construction of Tetrahydrobenzo[b]pyran and Chromeno[2,3-b]quinoline Derivatives

  摘要：

  Regioselective synthesis of functionalized tetrahydrobenzo[b]pyrans has been developed by multi-component reactions (MCRs) and tandem [3 + 3] annulations of beta-benzoylthioacetanilides or beta-(2-haloaroyl)thioacetanilides as valuable sources with aromatic aldehydes and 5,5-dimethy1-1,3-cyclohexanedione catalyzed by triethylamine. This MCR followed by a postcondensation cyclization via an intramolecular SNAr in the presence of K2CO3 led to an unprecedented novel chromeno-[2,3-b]quinoline framework containing an important chromene moiety in good yields. The reactions were very mild, convenient, and o-selective to form new fused tetracyclic target molecules.

  DOI：

  10.1021/jo101902z