2-tert-butyl-4-chloro-5-hydroxynaphtho[2,1-d]oxazole | 1264259-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-tert-butyl-4-chloro-5-hydroxynaphtho[2,1-d]oxazole
• 英文别名: 2-Tert-butyl-4-chlorobenzo[g][1,3]benzoxazol-5-ol
• CAS: 1264259-50-8
• 化学式: C₁₅H₁₄ClNO₂
• 分子量: 275.735
• InChiKey: ZILOGZCVJZKTFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-tert-butyl-4-chloro-5-hydroxynaphtho[2,1-d]oxazole 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以35%的产率得到2-tert-butylnaphtho[2,3-d]oxazole-4,9-dione
  参考文献：
  名称：

  Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds

  摘要：

  Treatment of 3-substituted 2-amino-1,4-naphthoquinones 3 with an aldehyde in a solution of hydrobromic acid in acetic acid led to 2,4-disubstituted naphtho[2,1-d]oxazol-5-ols. The outcome of this simple conversion is even more remarkable in view of the very similar reactions reported in literature, which all give rise to completely different products. Furthermore, the acquired naphthoxazoles 5-11 could be oxidatively ring opened by means of PIFA or CAN into a series of N-acylated 2-amino-1,4-naphthoquinones. A synthetic pathway towards 2-substituted naphtho[2,3-d]oxazole-4,9-diones was also disclosed as the outcome of CAN mediated oxidation of a 4-chloronaphtho[2,1-d]oxazol-5-ol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.082
• 作为产物：
  描述：

  2-氨基-3-氯-1,4-萘醌 、 特戊醛 在 氢溴酸 、 溶剂黄146 作用下， 以97%的产率得到2-tert-butyl-4-chloro-5-hydroxynaphtho[2,1-d]oxazole
  参考文献：
  名称：

  Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds

  摘要：

  Treatment of 3-substituted 2-amino-1,4-naphthoquinones 3 with an aldehyde in a solution of hydrobromic acid in acetic acid led to 2,4-disubstituted naphtho[2,1-d]oxazol-5-ols. The outcome of this simple conversion is even more remarkable in view of the very similar reactions reported in literature, which all give rise to completely different products. Furthermore, the acquired naphthoxazoles 5-11 could be oxidatively ring opened by means of PIFA or CAN into a series of N-acylated 2-amino-1,4-naphthoquinones. A synthetic pathway towards 2-substituted naphtho[2,3-d]oxazole-4,9-diones was also disclosed as the outcome of CAN mediated oxidation of a 4-chloronaphtho[2,1-d]oxazol-5-ol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.082

文献信息

• Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds
  作者：Sam Van Aeken、Jurgen Deblander、Johan De Houwer、Timothy Mosselmans、Kourosch Abbaspour Tehrani

  DOI：10.1016/j.tet.2010.10.082

  日期：2011.1

  Treatment of 3-substituted 2-amino-1,4-naphthoquinones 3 with an aldehyde in a solution of hydrobromic acid in acetic acid led to 2,4-disubstituted naphtho[2,1-d]oxazol-5-ols. The outcome of this simple conversion is even more remarkable in view of the very similar reactions reported in literature, which all give rise to completely different products. Furthermore, the acquired naphthoxazoles 5-11 could be oxidatively ring opened by means of PIFA or CAN into a series of N-acylated 2-amino-1,4-naphthoquinones. A synthetic pathway towards 2-substituted naphtho[2,3-d]oxazole-4,9-diones was also disclosed as the outcome of CAN mediated oxidation of a 4-chloronaphtho[2,1-d]oxazol-5-ol. (C) 2010 Elsevier Ltd. All rights reserved.