Phenyl-(3-cyan-propyl)-sulfon | 90922-18-2

• 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: Phenyl-(3-cyan-propyl)-sulfon
• 英文别名: 4-benzenesulfonyl-butyronitrile；4-(Benzenesulfonyl)butanenitrile
• CAS: 90922-18-2
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: SYRDQLMWFSXXMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苯基巯基丁腈 在 过氧乙酸 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 生成 Phenyl-(3-cyan-propyl)-sulfon
  参考文献：
  名称：

  Synthesis and Some Derivatives of 3-Butenenitrile

  摘要：

  DOI：

  10.1021/jo01069a028

文献信息

• Electrocatalytic reactions: anion radical cyclobutanation reactions and electrogenerated base reactions
  作者：Greg A.N. Felton

  DOI：10.1016/j.tetlet.2007.11.171

  日期：2008.1

  Intermolecular anion radical [2+2] cyclobutanation reactions have been observed between vinyl sulfones and vinyl/propenyl ketones. The products are novel and formed electrocatalytically, although yields are at best modest (11–45%). Competing mechanisms are discussed. Additionally, the electrochemical reduction of vinyl alkyl sulfones in acetonitrile leads to near quantitative formation of cyanomethylation

  乙烯基砜和乙烯基/丙烯基酮之间已观察到分子间阴离子自由基[2 + 2]环丁烷化反应。这些产品是新颖的，并且可以通过电催化形成，尽管产率最高（11-45％）。讨论了竞争机制。另外，乙腈中乙烯基烷基砜的电化学还原导致氰基甲基化产物氰基砜的定量形成。一步法具有超过三十的电催化因子。
• Copper‐Catalyzed Radical Cross‐Coupling of Oxime Esters and Sulfinates for Synthesis of Cyanoalkylated Sulfones
  作者：Xue‐Song Zhou、Ying Cheng、Jun Chen、Xiao‐Ye Yu、Wen‐Jing Xiao、Jia‐Rong Chen

  DOI：10.1002/cctc.201901695

  日期：2019.11.7

  Sulfones and alkylnitriles play a significant role in both organic and medicinal chemistry, as versatile synthetic building blocks and privileged pharmacophores in many natural products and bioactive compounds. Herein, a room‐temperature, copper‐catalyzed radical cross‐coupling of redox‐active cycloketone oxime esters and sulfinate salts is described for the first time. Key to the success of this process

  砜和烷基腈在有机和药物化学中均起着重要作用，它是许多天然产物和生物活性化合物中的通用合成构件和特权药效团。本文首次描述了氧化还原活性环酮肟酯和亚磺酸盐在室温下铜催化的自由基交叉偶联。该过程成功的关键在于催化生成环状亚氨基自由基，并随后进行开环CC键裂解。然后将所得的氰基烷基自由基与亲核亚磺酸盐交叉偶联，形成氰基烷基化砜。
• One-Pot Synthesis of Aryl Sulfones from Organometallic Reagents and Iodonium Salts
  作者：Natalie Margraf、Georg Manolikakes

  DOI：10.1021/jo5027518

  日期：2015.3.6

  A transition-metal-free arylation of lithium, magnesium, and zinc sulfinates with diaryliodonium salts is described. The sulfinic acid salts were prepared from the reaction of the corresponding organometallic reagents and sulfur dioxide. Combination of the three single steps (preparation of the organometallic compound, sulfinate formation, and arylation) leads to a one-pot sequence for the synthesis

  描述了锂，镁和锌亚磺酸盐与二芳基碘鎓盐的无过渡金属芳基化。亚磺酸盐是由相应的有机金属试剂与二氧化硫反应制得的。三个单一步骤（有机金属化合物的制备，亚磺酸盐的形成和芳基化）的组合产生了从简单起始原料合成芳基砜的一锅法序列。已经研究了不对称二芳基碘鎓盐的化学选择性。将讨论这种方法的潜力和局限性。