1-Methylethenyl 4-methylphenyl sulfone | 67605-02-1

• 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: 1-Methylethenyl 4-methylphenyl sulfone
• 英文别名: 2-(4-tolylsulfonyl)propene；isopropenyl-p-tolyl sulfone；Isopropenyl-p-tolyl-sulfon；Isopropenyl-(p-tolyl)-sulfon；p-Tolyl-isopropenylsulfon；Isopropenyl-vinylsulfon；1-Methyl-4-(1-methyl-ethnenylsulphonyl)benzene；1-methyl-4-prop-1-en-2-ylsulfonylbenzene
• CAS: 67605-02-1
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: FNWOMDYVPDCDJB-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  177 °C(Press: 5 Torr)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 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

• 作为反应物：
  描述：

  1-Methylethenyl 4-methylphenyl sulfone 在 /BRN= 102438/ 作用下， 以 乙醇 为溶剂， 生成 1-[2-(toluene-4-sulfonyl)-propyl]-piperidine
  参考文献：
  名称：

  消除-加法。第十二部分。胺加到烯基，烯基和炔基对甲苯基砜上的速率

  摘要：

  对于在乙醇中于5至45°的温度下的反应，已经确定了向一系列αβ-不饱和胺中添加胺的速率。

  DOI：

  10.1039/j29670000351
• 作为产物：
  描述：

  2-(toluene-4-sulfonyl)-propionic acid 在 聚合甲醛 、 二乙胺 作用下， 生成 1-Methylethenyl 4-methylphenyl sulfone
  参考文献：
  名称：

  The Preparation of Unsaturated Sulfones by Condensation Reactions¹

  摘要：

  DOI：

  10.1021/ja01159a005

文献信息

• 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。
• Gold-Catalyzed Intermolecular CS Bond Formation: Efficient Synthesis of α-Substituted Vinyl Sulfones
  作者：Yumeng Xi、Boliang Dong、Edward J. McClain、Qiaoyi Wang、Tesia L. Gregg、Novruz G. Akhmedov、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1002/anie.201310142

  日期：2014.4.25

  A general method for the synthesis of α‐substituted vinyl sulfones makes use of a combination of a triazole gold complex and gallium triflate. This efficient CS bond formation between simple terminal alkynes and sulfinic acids provides access to various α‐substituted vinyl sulfones.

  合成α-取代乙烯基砜的一般方法是结合使用三唑金配合物和三氟甲磺酸镓。简单的末端炔烃与亚磺酸之间的这种有效的CS键形成提供了接触各种α-取代的乙烯基砜的途径。
• A General Synthetic Method for α-Methylene Compounds by the Palladium-Catalyzed Decarboxylation-Deacetoxylation of Allyl α-Acetoxymethylcarboxylates Substituted by an Electron-Withdrawing Group at α-position
  作者：Jiro Tsuji、Mohammad Nisar、Ichiro Minami

  DOI：10.1246/cl.1987.23

  日期：1987.1.5

  Allyl α-acetoxymethylcarboxylates substituted by ester, amide, nitro, cyano, and sulfonyl groups at α-position undergo smooth palladium-catalyzed decarboxylation-deacetoxylation under mild neutral conditions to afford corresponding α-methylene compounds in high yields.

  α-位被酯、酰胺、硝基、氰基和磺酰基取代的α-乙酰氧基甲基羧酸烯丙酯在温和的中性条件下进行顺利的钯催化脱羧-脱乙酰氧基化，以高产率得到相应的α-亚甲基化合物。
• A CONVENIENT METHOD FOR THE PREPARATION OF α-ALKYLATED VINYLIC SULFONES AND THEIR CONVERSION TO ALLYLIC SULFONES
  作者：Katsuhiko Inomata、Yuhji Tanaka、Shin-ichi Sasaoka、Hideki Kinoshita、Hiroshi Kotake

  DOI：10.1246/cl.1986.341

  日期：1986.3.5

  sulfones, which were readily available by the addition of pyrrolidine to vinylic or allylic sulfones, were converted to the corresponding α-alkylated vinylic sulfones through α-alkylation followed by elimination of pyrrolidino group. Some of the α-alkylated vinylic sulfones were further transformed to the corresponding allylic sulfones.

  2-吡咯烷烷基对甲苯基砜很容易通过将吡咯烷加成到乙烯基或烯丙基砜中而获得，通过 α-烷基化随后消除吡咯烷基，转化为相应的 α-烷基化乙烯基砜。一些α-烷基化乙烯基砜进一步转化为相应的烯丙基砜。
• SYNTHESIS OF SUBSTITUTED VINYL SULFONES VIA DEACYLATION
  作者：Hiroshi Kotake、Katsuhiko Inomata、Manabu Sumita

  DOI：10.1246/cl.1978.717

  日期：1978.7.5

  It was found that the anions of β-ketosulfones reacted with formaldehyde to give the corresponding vinyl sulfones via deacylation, which provides a new preparative method for olefinic bonds.

  研究发现，β-酮砜阴离子与甲醛反应，通过脱酰基化生成相应的乙烯基砜，为烯烃键提供了新的制备方法。