3,7-Dihydroxy-6H-dibenzopyran-6-one | 131086-97-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3,7-Dihydroxy-6H-dibenzopyran-6-one
• 英文别名: 3,7-dihydroxy-6H-benzo[c]chromen-6-one；6H-Dibenzo(b,d)pyran-6-one, 3,7-dihydroxy-；3,7-dihydroxybenzo[c]chromen-6-one
• CAS: 131086-97-0
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: CJXANWCSMBKJHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二甲氧基溴苯 在 四(三苯基膦)钯 三溴化硼 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 36.0h， 生成 3,7-Dihydroxy-6H-dibenzopyran-6-one
  参考文献：
  名称：

  Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic acid

  摘要：

  A general regiospecific synthesis of dibenzo[b,d]pyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I). The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7. BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8. In this manner, the naturally occurring dibenzopyranones 1a, autumnariol (1c), and the heterocyclic analogue 13 (Scheme III) were efficiently prepared.

  DOI：

  10.1021/jo00012a004

文献信息

• Domino Reactions of 1,3-Bis-Silyl Enol Ethers with Benzopyrylium Triflates: Efficient Synthesis of Fluorescent 6H-Benzo[c]chromen-6-ones, Dibenzo[c,d]chromen-6-ones, and 2,3-Dihydro-1H-4,6-dioxachrysen-5-ones
  作者：Bettina Appel、Nehad N. R. Saleh、Peter Langer

  DOI：10.1002/chem.200501024

  日期：2006.1.23

  condensation of 1,3-bis-silyl enol ethers with benzopyrylium triflates, generated in situ by the reaction of chromones with Me3SiOTf, afforded functionalized 2,3-dihydrobenzopyrans; treatment of the latter with NEt3 or BBr3 resulted in a domino retro-Michael-aldol-lactonization reaction and the formation of a variety of 7-hydroxy-6H-benzo[c]chromen-6-ones. The hydroxy group was functionalized by using Suzuki

  1，3-双甲硅烷基烯醇醚与苯并吡啶三氟甲磺酸酯的缩合反应是通过色酮与Me3SiOTf的反应原位生成的，提供了官能化的2，3-二氢苯并吡喃。用NEt 3或BBr 3处理后者会导致多米诺骨牌的迈克尔-迈克尔-醛缩内酰胺化反应，并形成多种7-羟基-6H-苯并[c] chromen-6-。通过使用Suzuki交叉偶联反应使羟基官能化。报道的方法学被应用于天然产物秋天水芹酚和一种新的荧光染料的合成，该荧光染料显示出有希望的光学性质。通过将色酮与包含一个偏氯基团的1,3-双甲硅烷基烯醇醚缩合，多米诺复古迈克尔-醛醇内酯化和苯甲酸酯化反应制得2,3-二氢-1H-4,6-二氧杂环戊烯-5-酮分子内威廉姆森反应。
• Synthesis of 7-hydroxydibenzopyran-6-ones <i>via</i> benzannulation of coumarins
  作者：H. Surya Prakash Rao、M. Prabakaran、Nandurka Muthanna

  DOI：10.1039/d2ob01203k

  日期：——

  We have successfully demonstrated a facile synthesis of a variety of 7-hydroxydibenzopyran-6-ones via a two-step protocol from 3-acylcoumarins having a latent Nazarov dienone functionality. Condensation of 3-acylcoumarins and ethyl cyanoacetate under basic (wet K2CO3) and microwave irradiation conditions followed by decarboethoxylative aromatization with Br2 or DDQ furnished dibenzopyran-6-ones in

  我们已经成功地证明了通过两步法从具有潜在纳扎罗夫二烯酮功能的 3-酰基香豆素中轻松合成各种 7-羟基二苯并吡喃-6-酮。3-酰基香豆素和氰基乙酸乙酯在碱性（湿 K 2 CO 3）和微波辐照条件下缩合，然后用 Br 2或 DDQ 脱碳乙氧基芳构化，以高产率提供二苯并吡喃-6-酮。C环的形成dibenzopyran-6-one 基序的主要依赖于活性亚甲基化合物和香豆素上的 C7 取代。二苯并吡喃-6-酮中的 Ar-Br 或 ArOTf 取代被用于钯催化的 Suzuki 与多种芳基硼酸偶联以增加结构多样性。C10 氰基二苯并吡喃-6-酮的还原脱氰提供了尿石素 A 的一些异构体。
• ALO, B. I.;KANDIL, A.;PATIL, P. A.;SHARP, M. J.;SIDDIGUI, M. A.;SNIECKUS,+, J. ORG. CHEM., 56,(1991) N2, C. 3763-3768
  作者：ALO, B. I.、KANDIL, A.、PATIL, P. A.、SHARP, M. J.、SIDDIGUI, M. A.、SNIECKUS,+

  DOI：——

  日期：——
• Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic acid
  作者：B. I. Alo、A. Kandil、P. A. Patil、M. J. Sharp、M. A. Siddiqui、Victor Snieckus、P. D. Josephy

  DOI：10.1021/jo00012a004

  日期：1991.6

  A general regiospecific synthesis of dibenzo[b,d]pyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I). The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7. BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8. In this manner, the naturally occurring dibenzopyranones 1a, autumnariol (1c), and the heterocyclic analogue 13 (Scheme III) were efficiently prepared.