2,3-diphenylbenzo[de]chromene | 1241954-63-1

• 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: 2,3-diphenylbenzo[de]chromene
• 英文别名: 3,4-Diphenyl-2-oxatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaene；3,4-diphenyl-2-oxatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaene
• CAS: 1241954-63-1
• 化学式: C₂₄H₁₆O
• 分子量: 320.39
• InChiKey: OMAPYHYJRXGHPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  萘酚 、 二苯基乙炔 在 dichloro[1,3-di(ethoxycarbonyl)-2,4,5-trimethylcyclopentadienyl]rhodium(III) dimer 、 silver(I) acetate 、 copper(II) acetate monohydrate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以62%的产率得到2,3-diphenylbenzo[de]chromene
  参考文献：
  名称：

  缺电子铑 (III) 催化剂加速 1-萘酚与炔烃的氧化 [4 + 2] 环化

  摘要：

  1,3-二乙氧基羰基-2,4,5-三甲基环戊二烯基(Cp E )铑( III )配合物在温和条件下对1-萘酚与内炔烃的催化氧化环化表现出高效。DFT 计算表明，协同金属化去质子化和还原消除步骤的较低活化能是提高反应性的关键。

  DOI：

  10.1039/d1ob02181h

文献信息

• Electrochemical ruthenium-catalyzed alkyne annulations by C–H/Het–H activation of aryl carbamates or phenols in protic media
  作者：Ruhuai Mei、Julian Koeller、Lutz Ackermann

  DOI：10.1039/c8cc07732k

  日期：——

  Electrooxidative peri-C–H activation was accomplished by versatile ruthenium(II) catalysis in terms of C–H/N–H and C–H/O–H functionalization. Thus, alkyne annulations proved viable with ample scope by organometallic C–H activation. The sustainable electrocatalysis exploited electricity, thereby avoiding the use of toxic transition metals as sacrificial oxidants. The robust ruthenium(II)-electrocatalysis

  Electrooxidative围-C-H活化是由通用的钌（完成II）催化的C-H / N-H和C-H / O-H官能的条款。因此，通过有机金属的C–H活化，炔烃环行证明在足够的范围内是可行的。可持续的电催化利用电力，从而避免使用有毒的过渡金属作为牺牲氧化剂。鲁棒的钌（II）电催化作用在质子醇/ H 2 O反应介质中，具有极好的位置，区域和化学选择性。
• Synthesis of Naphtho[1,8-<i>bc</i>]pyran Derivatives and Related Compounds through Hydroxy Group Directed CH Bond Cleavage under Rhodium Catalysis
  作者：Satoshi Mochida、Masaki Shimizu、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1002/asia.200900639

  日期：2010.4.1

  straightforward and efficient synthesis of naphtho[1,8‐bc]pyran derivatives and related polycyclic compounds is achieved by the rhodium‐catalyzed oxidative coupling of 1‐naphthols or other phenolic and alcoholic substrates with alkynes. In these annulation reactions, the hydroxy groups effectively act as the key function for the regioselective CH bond cleavage.

  萘并[1,8- bc ]吡喃衍生物和相关多环化合物的直接有效合成是通过1-萘酚或其他酚和醇底物与炔烃的铑催化氧化偶联而实现的。在这些环化反应中，羟基有效地充当区域选择性CH键裂解的关键功能。
• Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐ <i>de</i> ]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation
  作者：Kelu Yan、Xiaoyu Wang、Jiangwei Wen、Qiuyun Li、Ning Zhang、Shuyun Zhu、Xian‐En Zhao、Xiu Wang

  DOI：10.1002/ejoc.202201171

  日期：2022.11.18

  protocol possesses several notable features in terms of employing poorly developed iridium and environmentally friendly visible light as catalysts, the absence of external ligands and photosensitizers, atomic economy and site selectivity, and overcoming the chelation of the carbonyl in coumarin skeleton to the iridium catalyst.

  已经开发了羟基导向的铱催化合成吡喃并 [ 2,3,4- de ]chromen-2-ones 并在蓝光照射下进一步硫属化。该方案在使用不发达的铱和环境友好的可见光作为催化​​剂、不存在外部配体和光敏剂、原子经济性和位点选择性以及克服香豆素骨架中羰基对铱催化剂的螯合等方面具有几个显着特征。
• Hydroxyl-Directed Ruthenium-Catalyzed C–H Bond Functionalization: Versatile Access to Fluorescent Pyrans
  作者：Vedhagiri S. Thirunavukkarasu、Margherita Donati、Lutz Ackermann

  DOI：10.1021/ol301387t

  日期：2012.7.6

  Hydroxyl-assisted oxidative annulations of alkynes were accomplished with an inexpensive ruthenium(II) complex, delivering fluorescent pyrans via highly site selective as well as chemo- and regioselective C-H/O-H bond functionalizations.
• Cobalt-Catalyzed, Hydroxyl-Assisted C–H Bond Functionalization: Access to Diversely Substituted Polycyclic Pyrans
  作者：Pratip K. Dutta、Mahesh Kumar Ravva、Subhabrata Sen

  DOI：10.1021/acs.joc.8b02446

  日期：2019.2.1

  Highly efficient oxidative annulation of alkynes furnished diversely substituted pyran[2,3,4-de] chromene-2-one derivatives and related polycycles in moderate to high yield. The reaction is catalyzed by nontoxic, air-stable, and inexpensive Cp*Co(CO)I-2 catalyst. The hydroxyl moiety at the substrate acts as the directing group for the C-H bond activation.