2-chloro-3-(trifluoromethyl)butane-1,4-diol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2-chloro-3-(trifluoromethyl)butane-1,4-diol
• 英文别名: 2-Chloro-3-(trifluoromethyl)butane-1,4-diol
• 化学式: C₅H₈ClF₃O₂
• 分子量: 192.566
• InChiKey: CKODNHJBCOFQQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 、 三氟甲烷磺酰氯 在 dipotassium hydrogenphosphate 、 tris(1,10-phenanthroline)ruthenium(II) dichloride 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以50%的产率得到2-chloro-3-(trifluoromethyl)butane-1,4-diol
  参考文献：
  名称：

  Vicinal Difunctionalization of Alkenes: Chlorotrifluoromethylation with CF₃SO₂Cl by Photoredox Catalysis

  摘要：

  Photoredox-catalyzed vicinal chlorotrifluoromethylation of alkene is described. In the presence of Ru(Phen)(3)Cl-2, CF3SO2Cl was used as a source for the CF3 radical and chloride ion under visible light irradiation. Various terminal and internal alkenes were transformed to their vicinal chlorotrifluoromethylated derivatives. Biologically active compounds were applied under the condition to obtain desired products, suggesting that the method could be feasible for late-stage modification in drug discovery.

  DOI：

  10.1021/ol403716t

文献信息

• Overcoming the Potential Window-Limited Functional Group Compatibility by Alternating Current Electrolysis
  作者：Sachini Rodrigo、Atanu Hazra、Jyoti P. Mahajan、Hien M. Nguyen、Long Luo

  DOI：10.1021/jacs.3c05802

  日期：2023.10.11

  such potential window-limited functional group compatibility. Using alkene heterodifunctionalization as a model system, we design and demonstrate a series of AC-driven reactions that add two functional groups sequentially and separately under the cathodic and anodic pulses, including chloro- and bromotrilfuoromethylation as well as chlorosulfonylation. We discovered that the oscillating redox environment

  电合成方法的官能团兼容性通常受其潜在反应窗口的限制。在这里，我们报道了交流电 （AC） 电解可以克服这种潜在的窗口受限官能团兼容性。使用烯烃异质二官能化作为模型系统，我们设计并演示了一系列 AC 驱动的反应，这些反应在阴极和阳极脉冲下依次和分别添加两个官能团，包括氯和溴苯醚甲基化以及氯磺酰化。我们发现，交流电解过程中的振荡氧化还原环境允许氧化还原活性官能团在上一步氧化或还原后再生。因此，即使氧化还原不稳定官能团（如吡咯、醌和芳基硫醚）落在反应电位窗口内，它们在交流电解条件下也能耐受，从而获得合成有用的产率。循环伏安法研究证实，产品产量受到氧化还原循环过程中起始材料再生程度的限制。我们的研究结果为提高电合成中的官能团相容性开辟了一条新途径，并显示了从伏安图特征预测交流电解下产物产率的可能性。
• Vicinal Difunctionalization of Alkenes: Chlorotrifluoromethylation with CF₃SO₂Cl by Photoredox Catalysis
  作者：Se Hwan Oh、Yashwardhan R. Malpani、Neul Ha、Young-Sik Jung、Soo Bong Han

  DOI：10.1021/ol403716t

  日期：2014.3.7

  Photoredox-catalyzed vicinal chlorotrifluoromethylation of alkene is described. In the presence of Ru(Phen)(3)Cl-2, CF3SO2Cl was used as a source for the CF3 radical and chloride ion under visible light irradiation. Various terminal and internal alkenes were transformed to their vicinal chlorotrifluoromethylated derivatives. Biologically active compounds were applied under the condition to obtain desired products, suggesting that the method could be feasible for late-stage modification in drug discovery.