2,3,7,8-tetramethoxy-6H-dibenzo[c,h]chromen-6-one | 111029-58-4

• 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: 2,3,7,8-tetramethoxy-6H-dibenzo[c,h]chromen-6-one
• 英文别名: 2,3,7,8-Tetramethoxynaphtho[1,2-c]isochromen-6-one
• CAS: 111029-58-4
• 化学式: C₂₁H₁₈O₆
• 分子量: 366.37
• InChiKey: ZXUPQWZBUPAOJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-Methylpapaverinium iodide 在 吡啶 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 134.0h， 生成 2,3,7,8-tetramethoxy-6H-dibenzo[c,h]chromen-6-one
  参考文献：
  名称：

  From Phenylacetylphenylacetic Acids and 1-Benzylisoquinolines to 6,11-Dihydrobenzo[b]naphtho[2,3-d]furan-6,11-diones, 6H-Dibenzo[c,h]chroman-6-ones and 7,12-Dihydro-5H-dibenzo[c,g]chroman-5,7,12-triones via 2-Phenyl-3-hydroxy-1,4-dihydro-1,4-naphthalenediones or 2-Phenyl-1-naphthols

  摘要：

  We describe the synthesis of 6,11-dihydrobenzo[b]naphtho[2,3-d]furane 6H-Dibenzo[c,h]chroman-6-ones and 7, 12-dihydro-5H-dibenzo[c,g]chroman-5,7, 12-triones from 2-(2'-phenyl)-3-hydroxy-1,4-dihydro-1,4-naphthalenediones or 2-phenyl-1-naphthols obtained from 2-(2'-bromophenylacetyl)-phenylacetic acids or l-benzylisoquinolines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00551-2

文献信息

• Dimethyl homophthalates to naphthopyrans: the total synthesis of arnottin I and the formal synthesis of (−)-arnottin II
  作者：Ravi Jangir、Narshinha P. Argade

  DOI：10.1039/c3ra45312j

  日期：——

  A simple and efficient 3-step synthetic protocol has been reported for dimethyl homophthalates to naphthopyrans. Starting from dimethyl 2,3-dimethoxyhomophthalate, a practical synthesis of arnottin I has been described via a base catalyzed mono-alkylation, the selective hydrolysis of an aliphatic ester moiety, two consecutive intramolecular cyclizations and an oxidative aromatization pathway with a very good overall yield. The involved intramolecular acylation followed by an associated enolative lactonization was the decisive step. The synthesis of dihydroarnottin I also completes the formal synthesis of (−)-arnottin II.

  据报道，从高邻苯二甲酸二甲酯到萘并吡喃的简单而有效的三步合成方案。从 2,3-二甲氧基高邻苯二甲酸二甲酯开始，通过碱催化的单烷基化、脂肪族酯部分的选择性水解、两个连续的分子内环化和氧化芳构化途径，描述了阿诺丁 I 的实际合成，具有非常好的总收率。所涉及的分子内酰化以及相关的烯醇内酯化是决定性的步骤。二氢arnottin I的合成也完成了()-arnottin II的正式合成。
• 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.
• 872. Synthetical experiments in the chelidonine–sanguinarine group of the alkaloids. Part IV
  作者：A. S. Bailey、C. R. Worthing

  DOI：10.1039/jr9560004535

  日期：——