2-allyl-3-(allyloxy)naphthalene-1,4-dione | 1604809-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-allyl-3-(allyloxy)naphthalene-1,4-dione
• CAS: 1604809-99-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: WMPPPJOPWQBXHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-allyl-3-(allyloxy)naphthalene-1,4-dione 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以54%的产率得到naphtho[2,3-b]oxepine-6,11(2H,5H)-dione
  参考文献：
  名称：

  Synthesis of fused chromene-1,4-naphthoquinones via ring-closing metathesis and Knoevenagel-electrocyclization under acid catalysis and microwave irradiation

  摘要：

  Two complementary methodologies involving olefin ring-closing metathesis and Knoevenagel-electrocyclization were utilized for the synthesis of alpha-xyloidones and fused chromene-1,4-naphthoquinones 5f-n and 6. The latter methodology was performed under acid catalysis or microwave irradiation allowing the synthesis of alpha-xyloidones 5f-j in moderate to good yield, which could not be obtained via the Knoevenagel-electrocyclization method. On the other hand, the lawsone bis-alkylation (C and 0) then RCM olefin enabled the preparation of simple xyloidone 5m-n and the oxepin-1,4-naphthoquinones 6. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.068
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.17h， 生成 2-allyl-3-(allyloxy)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of fused chromene-1,4-naphthoquinones via ring-closing metathesis and Knoevenagel-electrocyclization under acid catalysis and microwave irradiation

  摘要：

  Two complementary methodologies involving olefin ring-closing metathesis and Knoevenagel-electrocyclization were utilized for the synthesis of alpha-xyloidones and fused chromene-1,4-naphthoquinones 5f-n and 6. The latter methodology was performed under acid catalysis or microwave irradiation allowing the synthesis of alpha-xyloidones 5f-j in moderate to good yield, which could not be obtained via the Knoevenagel-electrocyclization method. On the other hand, the lawsone bis-alkylation (C and 0) then RCM olefin enabled the preparation of simple xyloidone 5m-n and the oxepin-1,4-naphthoquinones 6. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.068