7,8-dimethoxy-6H-dibenzo[c,h]chromen-6-one | 5653-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 7,8-dimethoxy-6H-dibenzo[c,h]chromen-6-one
• 英文别名: 7,8-dimethoxy-6H-benzo[d]naphtho[1,2-b]pyran-6-one；7,8-Dimethoxy-6H-benzo[d]naphtho[1,2-b]pyran-6-one；7,8-dimethoxynaphtho[1,2-c]isochromen-6-one
• CAS: 5653-54-3
• 化学式: C₁₉H₁₄O₄
• 分子量: 306.318
• InChiKey: NTOVAMRGKYVKJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-naphthyl 6-iodo-2,3-dimethoxybenzoate 在 bis(acetylacetonato)palladium(II) 、 sodium acetate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以79%的产率得到7,8-dimethoxy-6H-dibenzo[c,h]chromen-6-one
  参考文献：
  名称：

  通过钯介导的芳基-芳基偶联反应合成ArnottinI。

  摘要：

  6H-二苯并[b，d]吡喃-6-一，6H-苯并[d]萘并[1,2-b]吡喃-6-及其衍生物是通过钯介导的芳基芳基-芳基偶联反应制备的邻卤代苯甲酸酯。通过这种方法可以实现Arnottin I（1）的短时合成。

  DOI：

  10.1248/cpb.48.861

文献信息

• A Concise Synthesis of Arnottin I via Internal Biaryl Coupling Reaction Using Palladium Reagent
  作者：Takashi Harayama、Hirotake Yasuda

  DOI：10.3987/com-97-s23

  日期：——

  Total synthesis of arnottin I (1) was accomplished via the internal aryl-aryl coupling reaction of iodo-ester (2) by the palladium-assisted cyclization reaction.
• Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I
  作者：Sachin Madan、Chien-Hong Cheng

  DOI：10.1021/jo061477h

  日期：2006.10.1

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.
• Synthesis of Arnottin I through a Palladium-Mediated Aryl-Aryl Coupling Reaction.
  作者：Takashi HARAYAMA、Hirotake YASUDA、Toshihiko AKIYAMA、Yasuo TAKEUCHI、Hitoshi ABE

  DOI：10.1248/cpb.48.861

  日期：——

  6H-Dibenzo[b,d]pyran-6-one, 6H-benzo[d]naphtho[1,2-b]pyran-6-one, and their derivatives were prepared via the palladium mediated aryl-aryl coupling reaction of aryl ortho-halobenzoate. The short step synthesis of arnottin I(1) was achieved by this method.

  6H-二苯并[b，d]吡喃-6-一，6H-苯并[d]萘并[1,2-b]吡喃-6-及其衍生物是通过钯介导的芳基芳基-芳基偶联反应制备的邻卤代苯甲酸酯。通过这种方法可以实现Arnottin I（1）的短时合成。