5H-naphtho[1,2-c]chromene | 218-18-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5H-naphtho[1,2-c]chromene
• CAS: 218-18-8
• 化学式: C₁₇H₁₂O
• 分子量: 232.282
• InChiKey: ZSCNJMVVUFVCIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴苯基硼酸 在 sodium tetrahydroborate 、 trans-bis(triphenylphosphine)palladium dichloride 、 potassium tert-butylate 、 sodium acetate 、 palladium diacetate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 5H-naphtho[1,2-c]chromene
  参考文献：
  名称：

  Palladium-catalyzed and KO Bu-promoted Caryl–Oalcoholic coupling: an efficient one-pot synthesis of oxygen containing fused rings

  摘要：

  An efficient one-pot synthetic method has been developed for the synthesis of oxygen containing fused rings from 2'-bromo-biaryl-2-carbaldehyde via tandem reduction followed by palladium-catalyzed and (KOBu)-Bu-t-promoted C-aryl-O-alcoholic coupling. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.062

文献信息

• Intramolecular Palladium-Catalyzed Ring Opening of Oxabenzonorbornadienes with C₁-Tethered Aryl Halides
  作者：Samuel Koh、Austin Pounder、Elizabeth Brown、William Tam

  DOI：10.1021/acs.orglett.0c00900

  日期：2020.5.1

  The novel intramolecular ring opening of oxabenzonorbornadienes with C1-tethered aryl halides was investigated using palladium catalysts to form fused tetracyclic frameworks. The reaction was generally found to synthesize 1,2-dihydronaphthalen-1-ol products with mild selectivity but was capable of synthesizing dehydrated naphthalene products in excellent yield and selectivity. Substituent effects on

  使用钯催化剂形成稠合的四环骨架，研究了具有C1系芳基卤化物的氧杂苯并降冰片二烯的新型分子内开环。通常发现该反应以适度的选择性合成1,2-二氢萘-1-醇产物，但是能够以优异的产率和选择性合成脱水的萘产物。研究了对氧杂苯并降冰片二烯和对碘芳烃的取代作用以及不同系链长度的作用，几乎在所有情况下均观察到了有效的反应。总共报告了16个实例，产率从0到96％。
• Intramolecular Nickel-Catalyzed Ring-Opening Reactions of Oxabenzonorbornadienes with C₁ -Tethered Aryl Halides: An Improvement of Method
  作者：Samuel Koh、Austin Pounder、Elizabeth Brown、William Tam

  DOI：10.1002/ejoc.202000672

  日期：2020.8.9

  Oxabenzonorbornadienes with C1‐tethered aryl halides were found to rapidly undergo a ring‐opening reaction in the presence of NiCl2(PPh3)2, Zn, and MeCN to selectively form 1,2‐dihydronaphthalen‐1‐ol cores. 17 examples are shown with varying oxabenzonorbornadiene and iodoarene substitution, tether length, and halides, with yields up to 99 %.

  发现在NiCl 2（PPh 3）2，Zn和MeCN的存在下，带有C 1拴系的芳基卤化物的氧杂苯并降冰片二烯迅速发生开环反应，选择性地形成1,2-二氢萘-1-醇核。所示的17个实例具有不同的氧杂苯并降冰片二烯和碘芳烃取代基，系链长度和卤化物，产率高达99％。
• <i>ortho</i>-Nitro-substituted diaryliodonium salts enabled regioselective cyclization of arylcarboxylic acids toward 3,4-naphthocoumarins
  作者：Xu Liu、Limin Wang、Jianwei Han

  DOI：10.1039/d2ob01783k

  日期：——

  We herein report an efficient regioselective cascade of arylation and cyclization of arylcarboxylic acids via Pd(II)-activation of both C–I and vicinal C–NO2 bonds of ortho-nitro-substituted diaryliodonium salts.

  我们在此报道了通过Pd( II ) 激活邻硝基取代的二芳基碘盐的 C-I 和邻位 C-NO 2键，实现芳基羧酸芳基化和环化的有效区域选择性级联。
• Aryl–aryl cross-coupling reactions without reagents or catalysts: photocyclization of <i>ortho</i>-iodoaryl ethers and related compounds <i>via</i> triplet aryl cation intermediates
  作者：Wei Sun、Luke Wilding-Steele、Richard C. D. Brown、David C. Harrowven

  DOI：10.1039/d3cc03271j

  日期：——

  Cyclisations of benzyl ortho-iodoaryl ethers to benzo[c]chromenes can be effected without reagents or catalysts by irradiation with UVC under flow. Reactions proceed via triplet aryl cation generation, 5-exo and 3-exo-cyclisations, and rearomatisation. They have wide scope, are easy to effect and extend to a myriad of related ring systems.

  苄基邻碘芳基醚环化成苯并[ c ]色烯可以在没有试剂或催化剂的情况下通过在流动下用UVC照射来实现。反应通过三线态芳基阳离子生成、5-外型和3-外型环化以及重新芳构化进行。它们的范围很广，很容易实现并扩展到无数相关的环系统。