phenyl (E)-propenyl sulphide | 16336-50-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl (E)-propenyl sulphide
• 英文别名: phenyl (E)-(1-propenyl) sulfide；trans-1-propenyl phenyl sulfide；(E)-Phenyl prop-1-enyl sulfide；(E)-phenyl(prop-1-enyl)sulfane；(E)-phenyl 1-propenyl sulfide；phenyl 1-propenyl sulfide；(E)-Phenyl-1-propenylsulfide；[(E)-prop-1-enyl]sulfanylbenzene
• CAS: 16336-50-8；22103-05-5；15436-04-1
• 化学式: C₉H₁₀S
• 分子量: 150.244
• InChiKey: QAKDINZUNLASCF-KRXBUXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  phenyl (E)-propenyl sulphide 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-3-methyl-2-(phenylsulfonyl)-2-propenyl alcohol
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d
• 作为产物：
  描述：

  在 高氯酸 作用下， 以 甲醇 、 水 为溶剂， 以94%的产率得到phenyl (E)-propenyl sulphide
  参考文献：
  名称：

  苯硫酸锂对苯乙烯氧化物的区域和立体特异性裂解

  摘要：

  未取代的和α或βC取代的环氧锡烷酮与苯基硫化锂反应，生成由α-开环构型反转导致的区域和立体定义的α-苯硫基-β-羟基锡烷。在另一方面，α-或β-反式-甲硅烷epoxystannanes得到有规立构α-或通过在承载所述锡基团和随后的碳亲核攻击形成β甲硅烷基化vinylsulfides顺HOSnBu的β-消除3。两种类型的产品都是有机化学中有趣的合成子。

  DOI：

  10.1016/s0040-4039(01)01990-6

文献信息

• Proazaphosphatrane P(RNCH2CH2)3N (R=Me,i-Pr)-Catalyzed Isomerization of Allylaromatics, Allyl Phenyl Sulfide, Allyl Phenyl Sulfone, andbis-Allylmethylene Double Bond-Containing Compounds
  作者：Zhengkun Yu、Shenggang Yan、Guangtao Zhang、Wei He、Liandi Wang、Yu Li、Fanlong Zeng

  DOI：10.1002/adsc.200505224

  日期：2006.1

  Using a proazaphosphatrane catalyst, P(RNCH2CH2)3N (R=Me, i-Pr), allylaromatics and allyl phenyl sulfide were selectively isomerized to the corresponding vinyl isomers in yields up to >99% in CH3CN at 40 °C. Efficient transformation of allyl phenyl sulfone at ambient temperature afforded an isomerization/dimerization product in >95% yield. Conjugation of bis-allylmethylene double bond-containing compounds

  使用原氮杂磷杂环戊烷催化剂，将P（RNCH 2 CH 2）3 N（R = Me，i- Pr），烯丙基芳烃和烯丙基苯硫醚选择性异构化为相应的乙烯基异构体，在40° C的CH 3 CN中收率最高> 99％℃。在环境温度下烯丙基苯基砜的有效转化以> 95％的收率得到异构化/二聚产物。含双烯丙基亚甲基双键的化合物的共轭可得到相应的顺式，顺式-9,12-十八碳烯醇及其甲基醚的共轭异构体，收率最高可达97％，并且三甲基甲硅烷基的催化反应可制得甲硅烷基化/共轭产物。的以太顺式，顺式-9，12-十八碳烯基醇。基于在反应条件下在CD 3 CN或CH 3 CN中的1 H和31 P NMR监测的反应，讨论了反应机理。
• Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries
  作者：Shishi Lin、Shane D. Lies、Christopher S. Gravatt、Tehshik P. Yoon

  DOI：10.1021/acs.orglett.6b03545

  日期：2017.1.20

  The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach

  易于氧化的芳基硫醚部分的引入促进了烯烃自由基阳离子的光催化生成，该自由基阳离子与富电子反应伙伴进行各种环加成反应。随后，硫化物部分可以以无痕方式还原裂解，从而提供使用光氧化还原催化无法直接获得的产物。这种方法构成了一种新颖的氧化“氧化还原辅助”策略，提供了一种实用的方法来规避光氧化还原反应面临的基本热力学限制。
• First synthesis, X-ray structure analysis and reactions of alkenyltriphenylbismuthonium salts
  作者：Yoshihiro Matano、Masanori Yoshimune、Nagao Azuma、Hitomi Suzuki

  DOI：10.1039/p19960001971

  日期：——

  Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanide–alkenyltrialkylstannanes 3 in the presence of boron trifluoride–diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields. An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom. When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferered both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7–10 or the sulfides 12, 13, respectively. In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields. Action of KOBut on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24. A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.

  三苯基二氟化铋与烯基三甲基硅烷1或三甲基硅氰基-烯基三烷基锡烷3在三氟化硼-乙醚存在下反应，以中等至良好收率得到相应的烯基三苯基铋鎓四氟硼酸盐2。盐2e的X射线晶体学分析证实了中心铋原子扭曲的四面体几何结构。当与亚砜5或硫醇盐11处理时，盐2容易将乙烯基和苯基部分转移到这些亲核试剂上，分别得到砜7-10或硫化物12、13。在钯催化剂的存在下，盐2e与丙烯酸乙酯17发生 Heck 型反应，以中等收率得到二烯酸酯18和肉桂酸酯19。KOBut 对盐2b的作用产生了对甲苯乙炔22，而在苯乙烯23的存在下，盐2e的类似反应得到了环丙烷24。后一反应的 Hammett 研究表明，这些碱促进的反应中可能涉及一个烯基碳烯中间体。
• PREPARATION OF 1-ALKENYL PHENYL SULFIDES BY THE NICKEL(II)-COMPLEXES CATALYZED COUPLING REACTION OF 3-METHOXY-1-PHENYLTHIO-1-PROPENE WITH GRIGNARD REAGENTS
  作者：Hideyuki Sugimura、Hisashi Takei

  DOI：10.1246/cl.1984.1505

  日期：1984.9.5

  The reaction of 3-methoxy-1-phenylthio-1-propene with aryl and primary alkyl Grignard reagents in the presence of nickel(II)–phosphine complexes in benzene or toluene proceeded chemo- and regioselectively to give 1-alkenyl phenyl sulfides in high yields.

  3-甲氧基-1-苯硫基-1-丙烯与芳基和伯烷基格氏试剂在苯或甲苯中的镍（II）-膦配合物存在下进行化学和区域选择性反应，得到高浓度的 1-烯基苯基硫化物。产量。
• Hydride abstraction and regioselective insertion reaction at β C-H bond of alkyllithium by ethyl(phenylthio)methylene carbenoid
  作者：Toshiro Harada、Hisatomo Maeda、Akira Oku

  DOI：10.1016/s0040-4039(00)99034-8

  日期：——

  Study on the reaction of alkyllithium with 1-chloropropyl phenyl sulfide showed two novel reactions, the regioselective insertion and the hydride abstraction, at the β C-H bond of alkyllithium by ethyl(phenylthio)methylene carbenoid.

  对烷基锂与1-氯丙基苯硫醚反应的研究表明，在乙基锂的βCH键上，乙基（苯硫基）亚甲基类胡萝卜素对区域选择性插入和氢化物夺取两个新反应。