4-phenylbutane-1-sulfonyl fluoride | 1404225-72-4

• 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: 4-phenylbutane-1-sulfonyl fluoride
• 英文别名: 4-Phenylbutane-1-sulfonyl fluoride
• CAS: 1404225-72-4
• 化学式: C₁₀H₁₃FO₂S
• 分子量: 216.276
• InChiKey: WRECQDZLBBCTPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-phenyl-1-iodobutane 在 氟化铵 、 叔丁基锂 作用下， 以 乙醚 、 正己烷 、 丙酮 、 正戊烷 为溶剂， 反应 1.17h， 生成 4-phenylbutane-1-sulfonyl fluoride
  参考文献：
  名称：

  Sulfonyl Fluoride Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  Sulfonyl fluorides are known to inhibit esterases. Early work, from our laboratory has identified hexadecyl sulfonylfluoride (AM374) as a potent in vitro and in vivo inhibitor of fatty acid amide hydrolase (FAAH). We now report on later generation sulfonyl fluoride analogs that exhibit potent and selective inhibition of FAAH. Using recombinant rat and human FAAH, we show that 5-(4-hydroxyphenyl)pentanesulfonyl fluoride (AM3506) has similar inhibitory activity for both the rat and the human enzyme, while dilution assays and mass spectrometry analysis suggest that the compound is a covalent modifier for FAAH and inhibits its action in an irreversible manner. Our SAR results are highlighted by molecular docking of key analogs.

  DOI：

  10.1021/jm301205j

文献信息

• 一种制备烷基磺酰氟的方法
  申请人：上海应用技术大学

  公开号：CN113698325B

  公开（公告）日：2022-12-16

  本发明涉及一种制备烷基磺酰氟的方法，以烷基羧酸转化的还原活性酯为原料，二氧化硫替代试剂为二氧化硫源，亲电氟化试剂为氟源，在还原性金属还原及惰性气体保护条件下反应得到目标产物烷基磺酰氟。与现有技术相比，本发明合成方法简单，具有原位引入磺酰氟基团的选择性及较高产率，易于实现规模化生产。
• An Easy, General and Practical Method for the Construction of Alkyl Sulfonyl Fluorides
  作者：Xu Zhang、Wan‐Yin Fang、Ravindar Lekkala、Wenjian Tang、Hua‐Li Qin

  DOI：10.1002/adsc.202000515

  日期：2020.8.19

  and 3° alkyl iodides to ethenesulfonyl fluoride, employing Hantzsch ester as a hydrogen source at room temperature was developed. This method featured a wide substrate scope and great functional group compatibility, providing facile and robust process to alkyl sulfonyl fluorides including enzyme inhibitors, natural products and drugs derivatives in up to 99% yield. Further derivatization of resultant

  在室温下，使用汉茨sch酯作为氢源，开发了一种可见光诱导的将1°，2°和3°烷基碘还原加入乙磺酰氟的方法。该方法具有广泛的底物范围和出色的官能团相容性，可为烷基磺酰氟（包括酶抑制剂，天然产物和药物衍生物）提供简便而稳固的工艺，产率高达99％。还可以通过氟化硫交换（SuFEx）反应实现对生成的脂肪族磺酰氟的进一步衍生，以传递磺酸盐和磺酰胺作为药物化学的优先基序。
• Radical Hydro‐Fluorosulfonylation of Unactivated Alkenes and Alkynes
  作者：Peng Wang、Honghai Zhang、Mingqi Zhao、Shuangshuang Ji、Lu Lin、Na Yang、Xingliang Nie、Jinshuai Song、Saihu Liao

  DOI：10.1002/anie.202207684

  日期：2022.9.26

  Radical hydro-fluorosulfonylation of olefins has been successfully achieved by employing FABI as a FSO2-radical precursor and ODA as an organic photocatalyst. With this photocatalytic system, radical hydro-fluorosulfonylation of alkynes can also be realized with a unique, high Z-selectivity. Utilization of this method is further demonstrated in the late-stage modification of natural products and drug

  通过使用FABI作为FSO 2 -自由基前体和ODA作为有机光催化剂，已经成功地实现了烯烃的自由基氢氟磺酰化。使用这种光催化系统，炔烃的自由基氢氟磺酰化也可以以独特的高Z选择性实现。在天然产物的后期修饰和药物连接化学中进一步证明了该方法的利用。
• Copper-catalyzed direct decarboxylative fluorosulfonylation of aliphatic carboxylic acids
  作者：Ji-Tao Yi、Xiang Zhou、Qi-Long Chen、Zhi-Da Chen、Gui Lu、Jiang Weng

  DOI：10.1039/d2cc03221j

  日期：——

  emerging as key structural motifs in organic synthesis, medicinal chemistry, and materials science. Herein we report two efficient and complementary methods for direct decarboxylative fluorosulfonylation of carboxylic acids by the merging of copper catalysis with different N-centered HAT regents. A wide range of structurally diverse sulfonyl fluorides was readily accessed from primary, secondary, and tertiary

  磺酰氟正在成为有机合成、药物化学和材料科学中的关键结构基序。在这里，我们报告了两种有效且互补的方法，通过将铜催化与不同的以N为中心的 HAT 试剂相结合，对羧酸进行直接脱羧氟磺酰化。在温和条件下，一步即可从伯、仲和叔羧酸中轻松获得多种结构多样的磺酰氟。
• Aliphatic Sulfonyl Fluoride Synthesis via Decarboxylative Fluorosulfonylation of Hypervalent Iodine(III) Carboxylates
  作者：Caiyun Ou、Yinxia Cai、Yuyang Ma、Haozhen Zhang、Xiaoyu Ma、Chao Liu

  DOI：10.1021/acs.orglett.3c02652

  日期：2023.9.15

  photocatalytic decarboxylative fluorosulfonylation reaction of various hypervalent iodine(III) carboxylates in combination with 1,4-diazabicyclo[2.2.2]octane–bis(sulfur dioxide) adduct as a sulfonyl source and KHF2 as a desirable fluorine source via a radical sulfur dioxide insertion and fluorination strategy. A one-pot photocatalytic decarboxylative fluorosulfonylation reaction of various carboxylic acids mediated

  我们在此公开了各种高价碘(III)羧酸盐与作为磺酰源的1,4-二氮杂双环[2.2.2]辛烷-双(二氧化硫)加合物和作为所需氟源的KHF 2组合的光催化脱羧氟磺酰化反应，通过激进的二氧化硫插入和氟化策略。还实现了PhI(OAc) 2介导的多种羧酸的一锅光催化脱羧氟磺酰化反应。值得注意的是，这种转化可以在加热条件下进行，而不需要催化剂。