(E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-trifluoromethylbenzene | 1554271-53-2

• 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: (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-trifluoromethylbenzene
• 英文别名: (E)-1-chloro-4-((4-(trifluoromethyl)styryl)sulfonyl)benzene；1-[(E)-2-(4-chlorophenyl)sulfonylethenyl]-4-(trifluoromethyl)benzene
• CAS: 1554271-53-2
• 化学式: C₁₅H₁₀ClF₃O₂S
• 分子量: 346.757
• InChiKey: FNKUGOIXYKQKHO-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diethyl (((4-chlorophenyl)thio)methyl)phosphonate 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.0h， 生成 (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-trifluoromethylbenzene
  参考文献：
  名称：

  Discovery of Vinyl Sulfones as a Novel Class of Neuroprotective Agents toward Parkinson’s Disease Therapy

  摘要：

  Although the etiology of Parkinson's disease (PD) remains elusive, recent studies suggest that oxidative stress contributes to the cascade leading to dopaminergic (DAergic) neurodegeneration. The Nrf2, signaling is the main pathway responsible for cellular defense system against oxidative stress. Nrf2 is a transcription factor that regulates environmental stress response by inducing expression of antioxidant enzyme genes. We have synthesized novel vinyl sulfone derivatives. They exhibited a broad range of activities in inducing HO-1, whose gene expression is under the control of Nrf2. Among them, compound 12g was confirmed to activate Nrf2 and induce expression of the Nrf2-dependent antioxidant enzymes NQO1, GCLC, GLCM, and HO-1, at both mRNA and protein levels in DAergic neuronal cells. This was accompanied by protection of DAergic neurons in both in vitro and MPTP-induced in vivo models of PD. In addition, compound 12g effectively resulted in attenuation of the PD-associated behavioral deficits in the mouse model.

  DOI：

  10.1021/jm401788m

文献信息

• Air Induced Phosphoryl Radical Mediated Stereoselective Hydrosulfonylation of Alkynes <i>via</i> Halogen Atom Transfer: Ingress of <i>Z</i>-Vinyl Sulfones
  作者：Shashikant Tiwari、Manisha Kumari、Diwan S. Rawat

  DOI：10.1021/acs.orglett.4c00539

  日期：2024.3.22

  phosphoryl radical is well-known to participate in addition reactions with alkenes/alkynes. Here, we report a novel reaction mode of the phosphoryl radical where it participates in halogen atom transfer (XAT) with electron deficient vinyl halides instead of a facile addition reaction. Nevertheless, in comparison with aryl and alkyl halides, the exploitation of vinyl halides into a carbon radical via XAT

  众所周知，磷酰基参与与烯烃/炔烃的加成反应。在这里，我们报告了磷酰基自由基的一种新反应模式，其中它参与与缺电子乙烯基卤化物的卤素原子转移（XAT），而不是简单的加成反应。然而，与芳基卤化物和烷基卤化物相比，通过XAT 将卤乙烯转化为碳自由基的情况相当罕见。该方案提供了在环境友好的条件下直接氢磺酰化许多内部和末端炔烃以获得各种Z-乙烯基砜的机会。在露天产生磷酰基、以水为溶剂、优异的官能团相容性和优异的化学选择性是本方法的吸引人的特征。