2-(4-nitrobenzyl)tetrahydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-nitrobenzyl)tetrahydrofuran
• 英文别名: 2-[(4-Nitrophenyl)methyl]oxolane
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: ZIZCLJYDGHGEGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(4-nitrophenyl)pent-4-yn-1-ol 在 苄基三甲基氢氧化铵 、 palladium on activated charcoal 、 氢气 作用下， 以 N,N-二甲基甲酰胺 、 乙酸乙酯 为溶剂， 反应 0.03h， 以98%的产率得到2-(4-nitrobenzyl)tetrahydrofuran
  参考文献：
  名称：

  Catalytic and metal-free intramolecular hydroalkoxylation of alkynes

  摘要：

  Benzyltrimethylammonium hydroxide act as an efficient metal-free catalyst for the intramolecular hydroalkoxylation of alkynes. Notably, the use of microwave irradiation allowed reaction to operate in only two minutes. Under optimized reaction conditions, linear alkynes bearing aryl and heteroaryl substituents were successfully cyclized with good level of stereoselectivity. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2019.01.020

文献信息

• Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π‐Alkene Activation
  作者：Mathilde Rigoulet、Olivier Thillaye du Boullay、Abderrahmane Amgoune、Didier Bourissou

  DOI：10.1002/anie.202006074

  日期：2020.9.14

  possibility to combine oxidative addition of aryl iodides and π‐activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5‐, 6‐, and 7‐membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron‐rich aryl substrates, which are troublesome

  （MeDalphos）AuCl络合物通过Au I / Au III催化可有效实现烯烃与芳基碘的杂芳基化反应。首次证明了在金中结合芳基碘化物的氧化加成和烯烃的π-活化的可能性。该反应牢固且通用（> 30个实例，包括内部烯烃，5元，6元和7元环）。它是区域选择性的，专门导致反式加成产物。（P，N）金络合物在富电子芳基底物方面效率最高，这对于其他光氧化还原/氧化方法来说是麻烦的。此外，它还提供了从5外向内向6内向区域选择性的非常不同的转换 内部烯醇的Z和E异构体之间的环化。
• US6967205B1
  申请人：——

  公开号：US6967205B1

  公开（公告）日：2005-11-22
• Catalytic and metal-free intramolecular hydroalkoxylation of alkynes
  作者：Alexandre Jean、Jacques Rouden、Jacques Maddaluno、Michaël De Paolis、Jérôme Blanchet

  DOI：10.1016/j.tetlet.2019.01.020

  日期：2019.2

  Benzyltrimethylammonium hydroxide act as an efficient metal-free catalyst for the intramolecular hydroalkoxylation of alkynes. Notably, the use of microwave irradiation allowed reaction to operate in only two minutes. Under optimized reaction conditions, linear alkynes bearing aryl and heteroaryl substituents were successfully cyclized with good level of stereoselectivity. (C) 2019 Elsevier Ltd. All rights reserved.