(E)-1-(2-((4-fluorophenyl)sulfonyl)vinyl)-4-fluorobenzene | 1369434-63-8

• 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-fluorophenyl)sulfonyl)vinyl)-4-fluorobenzene
• 英文别名: (E)-1-fluoro-4-(2-((4-fluorophenyl)sulfonyl)vinyl)benzene；1-fluoro-4-[(E)-2-(4-fluorophenyl)sulfonylethenyl]benzene
• CAS: 1369434-63-8
• 化学式: C₁₄H₁₀F₂O₂S
• 分子量: 280.295
• InChiKey: YNBZHLIIMJKVSH-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl (4-fluorophenylthio)methylphosphonate 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-fluorophenyl)sulfonyl)vinyl)-4-fluorobenzene
  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

• Metal-free, one-pot highly selective synthesis of (E)-vinyl sulfones and sulfoxides via addition–oxidation of thiols with alkynes
  作者：Qicai Xue、Zhijie Mao、Yan Shi、Haibin Mao、Yixiang Cheng、Chengjian Zhu

  DOI：10.1016/j.tetlet.2012.01.135

  日期：2012.4

  We have developed a highly selective one-pot method for the synthesis of (E)-vinyl sulfones and sulfoxides from thiols with terminal alkynes. The sulfones and sulfoxides could be obtained with excellent selectivity in good isolated yields. It is simple, efficient and environmentally benign, and metal-free. The mechanism for the formation of the (E)-vinyl sulfones was also proposed.

  我们已经开发了一种高度选择性的一锅法，用于从具有末端炔烃的硫醇合成（E）-乙烯基砜和亚砜。可以以良好的选择性和良好的分离收率获得砜和亚砜。它简单，高效且对环境无害，并且不含金属。还提出了形成（E）-乙烯基砜的机理。
• Synthesis of Vinyl Sulfones via I₂ -mediated Alkene Sulfonylations with Thiosulfonates
  作者：Sang Joon Hwang、Pranab K. Shyam、Hye-Young Jang

  DOI：10.1002/bkcs.11426

  日期：2018.4

  sulfonylation strategy involving I2 and thiosulfonates, as sulfonyl‐group precursors, is reported for the synthesis of vinyl sulfones. Sulfonyl radicals are presumed to be generated from thiosulfonates, which subsequently react with styrene or cinnamic acid derivatives to afford a variety of vinyl sulfones under the described reaction conditions. Detailed conditions, the substrate scope, and mechanistic studies

  据报道，一种简单的磺酰化策略涉及I 2和作为磺酰基基团前体的硫代磺酸盐，用于合成乙烯基砜。推测磺酰基产生了磺酰基，其随后在描述的反应条件下与苯乙烯或肉桂酸衍生物反应以提供各种乙烯基砜。讨论了详细的条件，基材范围和机理研究。
• Discovery of Vinyl Sulfones as a Novel Class of Neuroprotective Agents toward Parkinson’s Disease Therapy
  作者：Seo Yeon Woo、Ji Hyun Kim、Mi Kyeong Moon、Se-Hee Han、Seul Ki Yeon、Ji Won Choi、Bo Ko Jang、Hyo Jung Song、Yong Gu Kang、Jin Woo Kim、Jaeick Lee、Dong Jin Kim、Onyou Hwang、Ki Duk Park

  DOI：10.1021/jm401788m

  日期：2014.2.27

  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.