(Z)-(but-2-en-1-ylsulfonyl)benzene | 89249-38-7

• 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: (Z)-(but-2-en-1-ylsulfonyl)benzene
• 英文别名: (but-2-en-1-ylsulfonyl)benzene；[(Z)-but-2-enyl]sulfonylbenzene
• CAS: 89249-38-7
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: ZXZCCQGNKNBXMW-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-丁炔基苯基砜 在 氯化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 以26%的产率得到(Z)-(but-2-en-1-ylsulfonyl)benzene
  参考文献：
  名称：

  Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride

  摘要：

  Propargylic sulfones can be cis-hydrogenated using commercial zinc powder and ammonium chloride in THF-water at room temperature, the major products being the corresponding (Z)-allylic sulfones. Other reducible groups (alkene, benzyloxy) are not affected. Allenylsulfones are implicated in one of the possible reaction pathways. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.099

文献信息

• Direct Oxidative Allylic and Vinylic Amination of Alkenes through Selenium Catalysis
  作者：Johanna Trenner、Christian Depken、Thomas Weber、Alexander Breder

  DOI：10.1002/anie.201303662

  日期：2013.8.19

  Bringing “N” into the game: The direct chemoselective nitrogenation of unactivated alkenes can be achieved through oxidative selenium catalysis (see scheme). This method provides a broad variety of allylic imides in yields of up to 89 % using N‐fluorobenzenesulfonimide (NFSI) as the terminal oxidant and nitrogen source. Furthermore, an unprecedented selenium‐catalyzed vinylic C(sp2)–H nitrogenation

  将“ N”带入游戏中：可以通过氧化硒催化（参见方案）实现未活化烯烃的直接化学选择氮化。使用N-氟苯磺酰亚胺（NFSI）作为末端氧化剂和氮源，此方法可提供高达89％的多种烯丙基酰亚胺。此外，还发现了前所未有的硒催化的乙烯基C（sp 2）–H氮化。
• Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides
  作者：Niall Collins、Robert Connon、Goar Sánchez‐Sanz、Paul Evans

  DOI：10.1002/ejoc.202001065

  日期：2020.10.22

  The efficient isomerisation of a range of γ‐azido substituted vinyl sulfones is reported. The corresponding vinyl azides are typically obtained with high levels of Z‐stereochemistry. An exception is when R is an α‐methyl substituent is present when the E‐vinyl azide was preferred.

  据报道，一系列γ-叠氮基取代的乙烯基砜得到了有效的异构化。相应的乙烯基叠氮化物通常以较高的Z立体化学含量获得。一个例外是，当优先使用E-乙烯基叠氮化物时，当R是一个α-甲基取代基时。
• Palladium-catalyzed substitution of allylic alcohols with sulfinate salts: A synthesis of bicalutamide
  作者：Yin-Jia Jhang、Chieh-Yu Chang、Yu-Huan Lin、Chein-Chung Lee、Yen-Ku Wu

  DOI：10.1016/j.tetlet.2021.153060

  日期：2021.6

  A method is presented for the direct substitution of allylic alcohols with sodium arylsulfinates. The process involves a cooperative action of palladium catalysts, phenylboronic acid and titanium tetraisopropoxide. By taking advantage of this protocol, we achieved a concise synthesis of bicalutamide, an anti-androgen compound for treating prostate cancer.

  提出了一种用芳基亚磺酸钠直接取代烯丙醇的方法。该过程涉及钯催化剂、苯基硼酸和四异丙醇钛的协同作用。通过利用该协议，我们实现了比卡鲁胺的简洁合成，比卡鲁胺是一种用于治疗前列腺癌的抗雄激素化合物。
• Oxidative Allylic Esterification of Alkenes by Cooperative Selenium-Catalysis Using Air as the Sole Oxidant
  作者：Stefan Ortgies、Christian Depken、Alexander Breder

  DOI：10.1021/acs.orglett.6b01130

  日期：2016.6.17

  A new metal-free catalysis protocol for the oxidative coupling of nonactivated alkenes with simple carboxylic acids has been established. This method is predicated on the cooperative interaction of a diselane and a photoredox catalyst, which allows for the use of ambient air or pure O2 as the terminal oxidant. Under the title conditions, a range of both functionalized and nonfunctionalized alkenes

  建立了一种新的无金属催化方案，用于非活化烯烃与简单羧酸的氧化偶联。该方法基于二硒烷和光氧化还原催化剂的协同相互作用，这允许使用环境空气或纯O 2作为末端氧化剂。在标题条件下，一定范围的官能化和非官能化烯烃都可以容易地转化为相应的烯丙基酯产物，具有良好的收率（高达89％）和优异的区域选择性以及良好的官能团耐受性。
• Carbon Dioxide-Promoted Telomerization of 1,2- and 1,3-Dienes with Benzenesulfinate Catalyzed by Palladium(0)^\eweq
  作者：Yoshio Inoue、Harukichi Hashimoto

  DOI：10.1246/bcsj.59.3705

  日期：1986.11

  The telomerization of 1,2- and 1,3-dienes with benzenesulfinate dihydrate catalyzed by palladium(0) has been promoted by the presence of carbon dioxide.

  以二氧化碳的存在促进了由钯(0)催化的1,2-和1,3-二烯与苯磺酸二水合物的端基化反应。