2,3,7-triphenylbenzo[b]oxepine | 1510865-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 2,3,7-triphenylbenzo[b]oxepine
• CAS: 1510865-12-9
• 化学式: C₂₈H₂₀O
• 分子量: 372.466
• InChiKey: RXLVHTNZCNVJPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-hydroxy-5-phenylbenzaldehyde 在 正丁基锂 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.25h， 生成 2,3,7-triphenylbenzo[b]oxepine
  参考文献：
  名称：

  Straightforward Assembly of Benzoxepines by Means of a Rhodium(III)-Catalyzed C–H Functionalization of o-Vinylphenols

  摘要：

  Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2](2) and Cu(OAc)(2). The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

  DOI：

  10.1021/ja410538w

文献信息

• Electrooxidative Rhodium‐Catalyzed [5+2] Annulations via C−H/O−H Activations
  作者：Yulei Wang、João C. A. Oliveira、Zhipeng Lin、Lutz Ackermann

  DOI：10.1002/anie.202016895

  日期：2021.3.15

  five‐ and six‐membered heterocycles. In contrast, we herein describe the first electrochemical metal‐catalyzed [5+2] cycloadditions to assemble valuable seven‐membered benzoxepine skeletons by C−H/O−H activation. The efficient alkyne annulation featured ample substrate scope, using electricity as the only oxidant. Mechanistic studies provided strong support for a rhodium(III/I) regime, involving a

  涉及温和过渡金属催化的 C−H 活化的电氧化环化已成为快速构建五元和六元杂环的变革策略。相比之下，我们在此描述了第一个电化学金属催化的[5+2]环加成反应，通过CH/O-H活化组装有价值的七元苯并氧杂环骨架。高效的炔成环反应具有充足的底物范围，使用电作为唯一的氧化剂。机理研究为铑（III/I）体系提供了强有力的支持，其中涉及苯并氧杂配位的铑（I）夹心络合物作为催化剂静止状态，通过阳极氧化将其重新氧化为铑（III）。
• Rh(<scp>iii</scp>)-catalyzed (5 + 2)-cycloaddition reactions of <i>ortho</i>-hydroxyethyl phenols with internal alkynes: efficient synthesis of benzoxepines
  作者：Pratiksha Bhorali、Jyotshna Phukon、Sanjib Gogoi

  DOI：10.1039/d3ob00170a

  日期：——

  An unprecedented (5 + 2)-cycloaddition reaction of ortho-hydroxyethyl phenol and internal alkyne was developed. This Rh(III)-catalyzed reaction provided benzoxepine derivatives which have very high biological significance. A wide range of ortho-hydroxyethyl phenols and internal alkynes were studied to provide the benzoxepines in high yields.

  开发了邻羟乙基苯酚和内炔烃的前所未有的 (5 + 2)-环加成反应。这种 Rh( III ) 催化的反应提供了具有非常高生物学意义的苯并氧庚因衍生物。研究了范围广泛的邻羟乙基苯酚和内部炔烃以提供高产率的苯并氧杂庚啶。