(+/-)-3a-n-butoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-one | 1173286-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (+/-)-3a-n-butoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-one
• 英文别名: 5-Butoxy-2-oxa-3-azatricyclo[7.3.1.05,13]trideca-1(12),3,7,9(13),10-pentaen-6-one；5-butoxy-2-oxa-3-azatricyclo[7.3.1.05,13]trideca-1(12),3,7,9(13),10-pentaen-6-one
• CAS: 1173286-08-2
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: TZJRUIZKKHJHCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-3a-n-butoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以84%的产率得到(+/-)-1-n-butoxy-8-hydroxy-2-oxo-1,2-dihydronaphthalene-1-carbonitrile
  参考文献：
  名称：

  Novel Thermal and Microwave-Assisted Facile Route to Naphthalen-2(1H)-ones via an Oxidative Alkoxylation-Ring-Opening Protocol

  摘要：

  Several novel 1,1-disubstituted-8-hydroxynaphthalen-2(1H)-ones have been efficiently synthesized via a two-step sequence from 2-hydroxy-1-naphthaldehyde oxime. The methodology involves oxidative ring closure and alkoxylation to 3a-alkoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-ones, followed by thermal ring-opening. Both thermal and microwave irradiation conditions were used. A novel one-pot reaction of oxime to 8-isopropoxynaphthalene-1,7-diol using microwave irradiation is also reported.

  DOI：

  10.1021/ol9008574
• 作为产物：
  描述：

  1-Formamido-2-naphthol 、 正丁醇 在 碘苯二乙酸 作用下， 反应 0.1h， 以63%的产率得到(+/-)-3a-n-butoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-one
  参考文献：
  名称：

  Novel Thermal and Microwave-Assisted Facile Route to Naphthalen-2(1H)-ones via an Oxidative Alkoxylation-Ring-Opening Protocol

  摘要：

  Several novel 1,1-disubstituted-8-hydroxynaphthalen-2(1H)-ones have been efficiently synthesized via a two-step sequence from 2-hydroxy-1-naphthaldehyde oxime. The methodology involves oxidative ring closure and alkoxylation to 3a-alkoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-ones, followed by thermal ring-opening. Both thermal and microwave irradiation conditions were used. A novel one-pot reaction of oxime to 8-isopropoxynaphthalene-1,7-diol using microwave irradiation is also reported.

  DOI：

  10.1021/ol9008574

文献信息

• Novel Thermal and Microwave-Assisted Facile Route to Naphthalen-2(1<i>H</i>)-ones via an Oxidative Alkoxylation-Ring-Opening Protocol
  作者：Chrysanthi Dolka、Kristof Van Hecke、Luc Van Meervelt、Petros G. Tsoungas、Erik V. Van der Eycken、George Varvounis

  DOI：10.1021/ol9008574

  日期：2009.7.16

  Several novel 1,1-disubstituted-8-hydroxynaphthalen-2(1H)-ones have been efficiently synthesized via a two-step sequence from 2-hydroxy-1-naphthaldehyde oxime. The methodology involves oxidative ring closure and alkoxylation to 3a-alkoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-ones, followed by thermal ring-opening. Both thermal and microwave irradiation conditions were used. A novel one-pot reaction of oxime to 8-isopropoxynaphthalene-1,7-diol using microwave irradiation is also reported.