(Z)-1-(Phenylthio)-2-butene | 36195-55-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-1-(Phenylthio)-2-butene
• 英文别名: Benzene, (2-butenylthio)-, (Z)-；[(Z)-but-2-enyl]sulfanylbenzene
• CAS: 36195-55-8
• 化学式: C₁₀H₁₂S
• 分子量: 164.271
• InChiKey: BNNLEMHAUPCSCL-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 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：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-(Phenylthio)-2-butene 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-but-2-en-1-yl phenyl sulfide
  参考文献：
  名称：

  Kimmelma, Reijo, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 5, p. 344 - 347

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-but-2-en-1-yl phenyl sulfide 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 (Z)-1-(Phenylthio)-2-butene
  参考文献：
  名称：

  Kimmelma, Reijo, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 5, p. 344 - 347

  摘要：

  DOI：

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。
• On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides
  作者：Clovis Peppe、Liérson Borges de Castro

  DOI：10.1139/v09-043

  日期：2009.5

  was examined. A practical one-pot method to prepare organyl phenyl chalcogenides from indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better for organyl halides capable to produce stable carbocations.

  检测了铟 (III) 苯硫属元素化物（硫属元素 = 硫、硒）对有机卤化物（有机基 = 烷基、烯丙基、苄基、酰基）的反应性。发现了一种从铟金属和二苯基二硫属元素化物制备有机苯基硫属元素化物的实用一锅法。偶联的范围相当广泛，通常对能够产生稳定碳正离子的有机卤化物效果更好。
• Phosphorus Functionalized Dendrimers and Hyperbranched Polymers: Is There a Need for Perfect Dendrimers in Catalysis?
  作者：Fabrizio Ribaudo、Piet W. N. M. Van Leeuwen、Joost N. H. Reek

  DOI：10.1560/ijc.49.1.79

  日期：2009.5

  In this paper we describe the facile and straightforward covalent functionalization of commercially available dendritic poly(propylenimine) and hyper‐branched poly(ethylenimine) with P‐containing functional groups. The P‐functionalized macromolecules have been applied as multivalent ligands in the Pd‐catalyzed allylic substitution reactions (batch and continuous process) using either morpholine or thiophenol as nucleophile. Palladium complexes of all described molecules are active in allylic substitution reactions. The PEI functionalized polymers appear more sensitive to small changes in the P/Pd ratio than the PPI analogues, but form catalysts that are more active. When used in a continuous flow process the macromolecules are completely retained by the nanofiltration membrane, while the catalytic activity decreases with time because of palladium depletion. This is more severe for the allylic thiolation, probably because of the stronger affinity of sulfur for palladium, facilitating palladium leaching.

  摘要 本文介绍了用含 P 的官能团对市售树枝状聚（丙烯亚胺）和超支化聚（乙烯亚胺）进行简便直接的共价官能化。含 P 官能团的大分子已作为多价配体应用于以吗啉或噻吩酚为亲核体的钯催化烯丙基取代反应（间歇和连续过程）中。所有所述分子的钯配合物在烯丙基取代反应中都很活跃。与 PPI 类似物相比，PEI 功能化聚合物似乎对 P/Pd 比率的微小变化更为敏感，但形成的催化剂活性更高。在连续流工艺中使用时，大分子会被纳滤膜完全截留，而催化活性则会随着时间的推移而降低，这是因为钯耗竭的缘故。烯丙基硫醇化的情况更为严重，这可能是因为硫与钯的亲和力更强，有利于钯的沥滤。
• Novel Synthetic Reactions Using Bis(2,2,2-trifluoroethoxy)diorganosulfuranes
  作者：Tomoya Kitazume、Nobuo Ishikawa

  DOI：10.1246/bcsj.53.2064

  日期：1980.7

  Alkoxy- or acyloxysulfuranes prepared in situ by the ligand exchange of bis(2,2,2-trifluoroethoxy)diorganosulfuranes with alcohols or carboxylic acids were found to behave as a potential alkylating or acylating reagent for the preparation of unsymmetrical sulfides, ketones, and esters.

  发现通过双（2,2,2-三氟乙氧基）二有机硫烷与醇或羧酸的配位交换原位制备的烷氧基或酰氧基硫烷可用作制备不对称硫化物、酮和酯的潜在烷基化或酰化试剂.
• Selective Condensation of [3-(Alkylthio)allyl]titanium Reagent with Carbonyl Compounds
  作者：Kyoji Furuta、Yoshihiko Ikeda、Noriyuki Meguriya、Nobuo Ikeda、Hisashi Yamamoto

  DOI：10.1246/bcsj.57.2781

  日期：1984.10

  [3-(Ethylthio)allyl]titanium reagent generated easily from allyl ethyl sulfides condensed with aldehydes to give erythro-β-hydroxy sulfides in highly regio- and stereoselective manner. In contrast, crotyl ethyl sulfide reacted with aldehydes affording δ-hydroxy vinyl sulfide exclusively. The substitution pattern of the starting sulfide can have a pronounced effect on the selectivity in this condensation reaction

  [3-(乙硫基)烯丙基]钛试剂很容易从烯丙基乙基硫化物与醛缩合生成赤型-β-羟基硫化物，以高度区域和立体选择性的方式。相比之下，巴豆基乙基硫醚与醛反应仅提供 δ-羟基乙烯基硫醚。起始硫化物的取代模式对该缩合反应的选择性有显着影响。获得的赤型-β-羟基硫化物立体选择性地转化为反式乙烯基环氧乙烷或 1,3-链二烯。