(E)-1-fluoro-4-(2-((4-methoxyphenyl)sulfonyl)vinyl)benzene | 1369434-64-9

• 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-fluoro-4-(2-((4-methoxyphenyl)sulfonyl)vinyl)benzene
• 英文别名: 1-fluoro-4-[(E)-2-(4-methoxyphenyl)sulfonylethenyl]benzene
• CAS: 1369434-64-9
• 化学式: C₁₅H₁₃FO₃S
• 分子量: 292.331
• InChiKey: DMRLKTKUKVAPGE-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl (((4-methoxyphenyl)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-fluoro-4-(2-((4-methoxyphenyl)sulfonyl)vinyl)benzene
  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。
• Decarboxylative sulfonylation of arylpropiolic acids with sulfinic acids: synthesis of (E)-vinyl sulfones
  作者：Jatuporn Meesin、Praewpan Katrun、Vichai Reutrakul、Manat Pohmakotr、Darunee Soorukram、Chutima Kuhakarn

  DOI：10.1016/j.tet.2016.01.042

  日期：2016.3

  Na2CO3 as a promoter and arenesulfinic acids as sulfonylating reagents. This simple and environmentally benign transformation offers an alternative approach and allows for easy and rapid synthesis of (E)-vinyl sulfones from arylpropiolic acids and arenesufinic acids.

  芳基丙酸的脱羧磺酰化已经通过简单地使用Na 2 CO 3作为促进剂和芳烃磺酸作为磺酰化试剂来实现。这种简单且对环境无害的转化提供了一种替代方法，并允许从芳基丙酸和戊烯二酸轻松快速地合成（E）-乙烯基砜。
• Aryldiazonium Salts and DABSO: A Versatile Combination for Three‐Component Sulfonylative Cross‐Coupling Reactions
  作者：Pritha Das、Subhodeep Das、Ranjan Jana

  DOI：10.1002/asia.202200085

  日期：2022.6

  A catalyzed synthesis of diarylsulfones with arylboronic acids and catalyst-free synthesis of arylvinyl and alkylvinyl sulfones from vinyl bronic acids or halides is reported.

  报道了用芳基硼酸催化合成二芳基砜和由乙烯基溴酸或卤化物无催化剂合成芳基乙烯基和烷基乙烯基砜。
• Multicomponent hydrosulfonylation of alkynes for the synthesis of vinyl sulfones
  作者：Lan Mei、Xiao-Rong Shu、Fa-Liang Liu、Jiao-Zhe Li、Jian-Feng Zhang、Keqi Tang、Wen-Ting Wei

  DOI：10.1039/d3gc02284f

  日期：——

  hydrosulfonylations of alkynes have provided straightforward strategies for the synthesis of vinyl sulfones, these methods still exhibit several drawbacks, such as the use of large amounts of transition metal catalysts or/and additional additives. Herein, we report an efficient and mild multicomponent reaction (MCR) for the preparation of vinyl sulfones achieved by carrying out hydrosulfonylation of alkynes with the

  乙烯基砜是重要的结构基序，在生物医学领域具有广泛的应用。尽管炔烃的氢磺酰化为乙烯基砜的合成提供了简单的策略，但这些方法仍然表现出一些缺点，例如使用大量过渡金属催化剂或/和额外的添加剂。在此，我们报道了一种高效且温和的多组分反应（MCR），通过用相应的芳基重氮盐 K 2 S 2 O 5对炔烃进行氢磺酰化来制备乙烯基砜。和苯硫酚在室温下，无需任何金属催化剂或添加剂。该转化是苯硫酚作为氢源与乙烯基自由基反应的第一个例子，具有高化学选择性和步骤经济的优点。值得注意的是，该方法也适用于脂肪族炔烃，规避了现有方法的局限性，并且克级实验顺利进行，证明了该方法的实用性。
• 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.