(+/-)-1-(4-benzyloxyphenyl)pent-4-en-1-ol | 470665-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-1-(4-benzyloxyphenyl)pent-4-en-1-ol
• 英文别名: 1-(4-Phenylmethoxyphenyl)pent-4-en-1-ol
• CAS: 470665-15-7
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: WUSGZBXGSWGIFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(4-benzyloxyphenyl)pent-4-en-1-ol 在 α-AD mix {K4[Fe(CN)6], OsO4, Na2CO3, (DHQ)2-PHAL} 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 以57%的产率得到(+/-)-1-(4-benzyloxyphenyl)-4,5-dihydroxypentan-1-one
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers

  摘要：

  New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.

  DOI：

  10.1002/1521-4184(200203)335:2/3<94::aid-ardp94>3.0.co;2-w
• 作为产物：
  描述：

  4-溴-1-丁烯 、 4-苄氧基苯甲醛 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以55%的产率得到(+/-)-1-(4-benzyloxyphenyl)pent-4-en-1-ol
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers

  摘要：

  New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.

  DOI：

  10.1002/1521-4184(200203)335:2/3<94::aid-ardp94>3.0.co;2-w

文献信息

• Cobalt-Catalyzed Stereoselective Synthesis of 2,5-<i>trans</i>-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies
  作者：Sajjad Ali、Henrique Milanezi、Tânia M. F. Alves、Cláudio Francisco Tormena、Marco A. B. Ferreira

  DOI：10.1021/acs.joc.8b00575

  日期：2018.8.3

  straightforward protocol integrating a sustainable approach for the synthesis of new 2,5-trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substituents, affording the corresponding 2,5-trans-THFs in high diastereoselectivity. A detailed mechanistic study using DFT calculation reveals details of the ligand-exchange

  描述了一个简单的协议，该协议集成了一种可持续方法，用于合成新的2,5-反-THF腈衍生物，可轻松实现其侧链支架的多样化。该反应容许不同的芳族和烷基取代基，以高非对映选择性提供相应的2，5-反-THF。使用DFT计算进行的详细机理研究揭示了配体交换步骤的详细信息，表明内球体syn进攻形成2，5-反式立体化学是最可能的途径，而排除了先前的阳离子自由基中间体。建议在均相裂解的基础上形成Co-C中间体，以得到先前提出的游离碳自由基中间体。
• Electrocatalytic Oxidative Hydrofunctionalization Reactions of Alkenes via Co(II/III/IV) Cycle
  作者：Fan Yang、Yi-Chen Nie、Han-Yuan Liu、Lei Zhang、Fanyang Mo、Rong Zhu

  DOI：10.1021/acscatal.1c05557

  日期：2022.2.18

  Here we disclose a general Co(II/III/IV) electrocatalytic platform for alkene functionalization. Driven by electricity, a set of the oxidative hydrofunctionalization reactions via hydrogen atom transfer were demonstrated without the need for stochiometric chemical oxidants. The scope of the reactions encompasses hydroalkoxylation, hydroacyloxylation, hydroarylation, semipinacol rearrangement, and deallylation

  在这里，我们公开了一种用于烯烃官能化的通用 Co(II/III/IV) 电催化平台。在电力驱动下，证明了一组通过氢原子转移的氧化氢官能化反应，不需要化学计量的化学氧化剂。反应范围包括加氢烷氧基化、加氢酰氧基化、加氢芳基化、半频哪醇重排和去烯丙基化。机理研究和立体化学证据支持涉及电化学生成的有机钴 (IV) 中间体的 ECEC 过程。这项工作通过超越 Co(I/II/III) 的常见氧化态，展示了 VB 12系统中电催化中反应性空间扩展的示例。
• Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers
  作者：Jürgen Krauß、D. Unterreitmeier

  DOI：10.1002/1521-4184(200203)335:2/3<94::aid-ardp94>3.0.co;2-w

  日期：2002.3

  New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.