ethyl 2-((tetrahydrofuran-2-yl)methyl)acrylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-((tetrahydrofuran-2-yl)methyl)acrylate
• 英文别名: Ethyl 2-(oxolan-2-ylmethyl)prop-2-enoate；ethyl 2-(oxolan-2-ylmethyl)prop-2-enoate
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: IPFICEOFBOJTPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟甲基丙烯酸乙酯 在 偶氮二异丁腈 、 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 31.0h， 生成 ethyl 2-((tetrahydrofuran-2-yl)methyl)acrylate
  参考文献：
  名称：

  Use of allylic triflones for allylation of C-H bonds

  摘要：

  Allylic triflones react with THF and cyclohexane and related molecules to undergo a trifluoromethyl radical mediated C-H functionalization reaction. Due to polar effects, the reactions benefit from the presence of electron-withdrawing group at the 2-position of the allylic triflones. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00775-8

文献信息

• Radical additions of acyclic and cyclic ethers to alkenes via an allyl transfer reaction involving phthalimido-N-oxyl radical
  作者：Shradha V. Patil、James M. Tanko

  DOI：10.1016/j.tet.2016.05.046

  日期：2016.12

  reactions are of widespread interest. We have previously demonstrated the functionalization of benzylic C–H bonds via an allyl transfer reaction using various allyl-phthalimido-N-oxyl substrates. In this work, we demonstrate the extension of our mild, metal-free, and neutral allyl transfer methodology to the direct functionalization of ethers. The C–H bond in α position to the ether oxygen in various

  合成化学家非常感兴趣的是，对廉价的起始原料进行直接功能化以产生复杂的增值产品。特别地，人们普遍关注廉价的商品分子的直接功能化，而传统上认为便宜的商品分子对已知反应呈惰性。我们以前通过使用各种烯丙基-邻苯二甲酰亚胺基-N的烯丙基转移反应证明了苄基CH键的功能化-氧基底物。在这项工作中，我们证明了将温和，无金属和中性的烯丙基转移方法扩展到醚的直接功能化。高产率地官能化了各种无环和环状醚中醚氧在α位置的C–H键，表明该转化的底物范围广。此外，实现了对称环状醚的选择性单官能化和不对称醚的区域选择性官能化，从而证明了该反应的进一步实用性。最后，进行了动力学链长测量，这为涉及邻苯二甲酰亚胺-N-氧基（PINO ）自由基的链过程的初始速率和效率提供了有价值的见解。
• Modular allylation of C(sp³)–H bonds by combining decatungstate photocatalysis and HWE olefination in flow
  作者：Luca Capaldo、Stefano Bonciolini、Antonio Pulcinella、Manuel Nuño、Timothy Noël

  DOI：10.1039/d2sc01581a

  日期：——

  the development of a modular synthetic sequence for the allylation of strong aliphatic C(sp3)–H bonds. Our sequence features the merger of two distinct steps to accomplish this goal, including a photocatalytic Hydrogen Atom Transfer and an ensuing Horner–Wadsworth–Emmons (HWE) reaction. This practical protocol enables the modular and scalable allylation of valuable building blocks and has been applied

  烯丙基的后期引入为合成有机化学家提供了后续多样化的机会，为快速进入新的化学空间提供了机会。在这里，我们报告了用于强脂肪族 C(sp 3 )–H 键烯丙基化的模块化合成序列的开发。我们的序列融合了两个不同的步骤来实现这一目标，包括光催化氢原子转移和随后的霍纳-沃兹沃斯-埃蒙斯 (HWE) 反应。这种实用的协议能够实现有价值构建模块的模块化和可扩展的烯丙基化，并已应用于结构复杂的分子。
• Catalytic Photoinduced Intramolecular Decarboxylative and Desulfonylative <i>sp</i>^<i>3</i> Allylation Enabled by Sulfinate Salts
  作者：Franz‐Lucas Haut、Riccardo S. Mega、Joan V. Estornell、Ruben Martin

  DOI：10.1002/anie.202304084

  日期：2023.7.10

  Herein, we describe a catalytic intramolecular decarboxylative/desulfonylative sp³ allylation triggered by sulfinate salts under light irradiation. The reaction is likely enabled by a non‐classical, radical‐polar crossover mechanism, allowing rapid and reliable access to valuable allyl architectures from readily accessible precursors. The protocol is characterized by its operational simplicity and scalability, employing abundant, commercially available catalysts.

  摘要在本文中，我们描述了一种在光照射下由亚硫酸盐引发的催化分子内脱羧/脱磺sp3烯丙基化反应。该反应可能是通过非经典性的自由基-极性交叉机制实现的，从而可以快速可靠地从容易获得的前体中获得有价值的烯丙基结构。该方案的特点是操作简单、可扩展性强，并采用了丰富的市售催化剂。
• Use of allylic triflones for allylation of C-H bonds
  作者：Jason Xiang、Jerry Evarts、Alexey Rivkin、Dennis P. Curran、P.L. Fuchs

  DOI：10.1016/s0040-4039(98)00775-8

  日期：1998.6

  Allylic triflones react with THF and cyclohexane and related molecules to undergo a trifluoromethyl radical mediated C-H functionalization reaction. Due to polar effects, the reactions benefit from the presence of electron-withdrawing group at the 2-position of the allylic triflones. (C) 1998 Elsevier Science Ltd. All rights reserved.