4-[Methyl-[4-(4-methylphenoxy)but-2-ynyl]amino]chromen-2-one | 357290-78-9

• 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: 4-[Methyl-[4-(4-methylphenoxy)but-2-ynyl]amino]chromen-2-one
• CAS: 357290-78-9
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: NPJUTPGUVYGZEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[Methyl-[4-(4-methylphenoxy)but-2-ynyl]amino]chromen-2-one 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 0.17h， 生成 3-Hydroxymethyl-1-methyl-2-p-tolyloxymethyl-1H-chromeno[4,3-b]pyrrol-4-one
  参考文献：
  名称：

  Synthesis of bioactive heterocycles: tandem reaction of 4-N-(4′-aryloxybut-2′-ynyl),N-methylaminocoumarin with 3-chloroperoxybenzoic acid

  摘要：

  A number of 4-N-(4'-aryloxybut-2'-ynyl).N-methylaminocoumarins (4a-e) on treatment with one equivalent of 3-chloroperoxybenzoic acid at 0-5degreesC for 10 min and then stirring at rt for 10 It afforded pyrrolo[3,2-c]coumarin derivatives in 70-75% yields. The 4-N-(4'-aryloxybut-2'-ynyl),N-methylaminocoumarins 4a-e were in turn prepared from 4-tosyloxycoumarin (2) and (4-arytoxybut-2-ynyl)-N-methylamine (3a-e). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00198-3
• 作为产物：
  描述：

  4-(4-toluenesulfonyloxy)coumarin 、 1-(4-methylphenoxy)-4-N-methylaminobut-2-yne 以 乙醇 为溶剂， 生成 4-[Methyl-[4-(4-methylphenoxy)but-2-ynyl]amino]chromen-2-one
  参考文献：
  名称：

  Synthesis of bioactive heterocycles: tandem reaction of 4-N-(4′-aryloxybut-2′-ynyl),N-methylaminocoumarin with 3-chloroperoxybenzoic acid

  摘要：

  A number of 4-N-(4'-aryloxybut-2'-ynyl).N-methylaminocoumarins (4a-e) on treatment with one equivalent of 3-chloroperoxybenzoic acid at 0-5degreesC for 10 min and then stirring at rt for 10 It afforded pyrrolo[3,2-c]coumarin derivatives in 70-75% yields. The 4-N-(4'-aryloxybut-2'-ynyl),N-methylaminocoumarins 4a-e were in turn prepared from 4-tosyloxycoumarin (2) and (4-arytoxybut-2-ynyl)-N-methylamine (3a-e). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00198-3

文献信息

• Studies of bioactive heterocycles: amino Claisen rearrangement of 4-N-(4-aryloxybut-2-ynyl),N-methylaminocoumarins
  作者：K.C Majumdar、T Bhattacharyya

  DOI：10.1016/s0040-4039(01)00656-6

  日期：2001.6

  Thermal amino-Claisen rearrangement of 4-N-(aryloxybut-2-ynyl), N-methyl-aminocoumarins (8a-e) in refluxing o-dichlorobenzene gave 4-aryloxymethylene-1-methyl-1,2,3-trihydropyrido[3,2-c][1]benzopyran-5-ones (9a-e) in 56-72% isolated yields. Substrates (8a-f) were prepared from 4-chlorocoumarin (6a,b) and N-(4-ary-loxybutynyl),N-methylamine (7a-f) in 68-77% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of bioactive heterocycles: tandem reaction of 4-N-(4′-aryloxybut-2′-ynyl),N-methylaminocoumarin with 3-chloroperoxybenzoic acid
  作者：K.C Majumdar、S.K Samanta

  DOI：10.1016/s0040-4039(02)00198-3

  日期：2002.3

  A number of 4-N-(4'-aryloxybut-2'-ynyl).N-methylaminocoumarins (4a-e) on treatment with one equivalent of 3-chloroperoxybenzoic acid at 0-5degreesC for 10 min and then stirring at rt for 10 It afforded pyrrolo[3,2-c]coumarin derivatives in 70-75% yields. The 4-N-(4'-aryloxybut-2'-ynyl),N-methylaminocoumarins 4a-e were in turn prepared from 4-tosyloxycoumarin (2) and (4-arytoxybut-2-ynyl)-N-methylamine (3a-e). (C) 2002 Elsevier Science Ltd. All rights reserved.