(E)-1-chloro-3-(2-((4-chlorophenyl)sulfonyl)vinyl)benzene | 76859-78-4

• 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: (E)-1-chloro-3-(2-((4-chlorophenyl)sulfonyl)vinyl)benzene
• 英文别名: 1-chloro-3-[(E)-2-(4-chlorophenyl)sulfonylethenyl]benzene
• CAS: 76859-78-4
• 化学式: C₁₄H₁₀Cl₂O₂S
• 分子量: 313.204
• InChiKey: QJIFZBGVZPHVAD-CMDGGOBGSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  492.7±45.0 °C(predicted)
• 密度：
  1.398±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  2

反应信息

• 作为反应物：
  描述：

  三甲基碘化锍 、 (E)-1-chloro-3-(2-((4-chlorophenyl)sulfonyl)vinyl)benzene 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以74.8%的产率得到
  参考文献：
  名称：

  Reddy, D. Bhaskar; Balaji, T.; Reddy, B. Venkataramana, Phosphorus and Sulfur and the Related Elements, 1983, vol. 17, p. 297 - 306

  摘要：

  DOI：
• 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-chloro-3-(2-((4-chlorophenyl)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

• 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。
• Synthesis of α,β-Ethylenic Sulfones
  作者：M. Seshapathi、Rao Naidu、D. Bhaskar Reddy

  DOI：10.1246/bcsj.48.1091

  日期：1975.3

  A series of new α,β-ethylenic sulfones were prepared by the condensation of p-chlorophenylsulfonylacetic acid with various aryl aldehydes. The UV and IR spectra of all these compounds were recorded. Their IR spectra exhibited medium to strong bands in the region 1000–975 cm−1, characteristic of trans ethylenic compounds.

  对氯苯基磺酰基乙酸与多种芳基醛缩合制备了一系列新的α，β-乙烯砜。记录了所有这些化合物的紫外和红外光谱。它们的红外光谱在 1000-975 cm-1 区域显示出中等到较强的条带，这是反式乙烯化合物的特征。
• 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。
• Reddy, D. Bhaskar; Sankaraiah, B.; Balaji, T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 7, p. 563 - 566
  作者：Reddy, D. Bhaskar、Sankaraiah, B.、Balaji, T.

  DOI：——

  日期：——