2-butenyl p-tolyl sulfone | 24931-66-6

• 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: 2-butenyl p-tolyl sulfone
• 英文别名: 1-<(4-methylphenyl)sulfonyl>but-2-ene；crotyl p-tolyl sulfone；1-(but-2-ene-1-sulfonyl)-4-methylbenzene；1-(but-2-en-1-ylsulfonyl)-4-methylbenzene；But-2-enyl-p-tolylsulfon；1-p-tosyl-2-butene；1-But-2-enylsulfonyl-4-methylbenzene
• CAS: 24931-66-6
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: WCTXVIZVJWOLBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-butenyl p-tolyl sulfone 在 溴 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 28.0h， 生成 (E)-1-methyl-3-tosyl-2-propenyl acetate
  参考文献：
  名称：

  A simple method for the synthesis of γ-functionalized vinyl and allyl sulfones

  摘要：

  The synthesis of gamma-functionalized vinyl sulfones 3 have been carried out directly starting from dibromides 2 derived from allyl sulfones 1 by reaction with different nucleophiles. The process is stereoselective affording compounds 3 with E configuration except in the case of methallylic derivatives. The regioisomeric gamma-functionalized allyl sulfones 4 were obtained from dibromides 2 or from vinyl sulfones 3, with Z configuration, except when triphenylphosphine was used as nucleophile, in this case the corresponding (E)-vinylphosphonium bromide 4al was obtained.

  DOI：

  10.1016/s0040-4020(01)86563-7
• 作为产物：
  描述：

  4-甲基苯基亚硫酰氯 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 30.5h， 生成 2-butenyl p-tolyl sulfone
  参考文献：
  名称：

  “Syn-Effect” in the Desilylation Reaction of γ-Silylated Allylic and Vinylic Sulfones

  摘要：

  研究发现，γ-硅烷化的烯丙基砜通过γ-硅烷化的（E）-乙烯基砜的脱硅反应，在DBU和H2O处理下得到相应的烯丙基砜。所得烯丙基砜的Z/E比率会根据γ-硅烷化砜的γ-取代基的不同而变化。这一立体化学结果可以通过“顺效应”来解释。

  DOI：

  10.1246/cl.2003.1158

文献信息

• One-Pot Synthesis of Substituted Tetrahydrocyclobuta[<i>a</i>]naphthalenes by Domino Aldol Condensation/Olefin Migration/Electrocyclization
  作者：Meng-Yang Chang、Ming-Hao Wu、Yeh-Long Chen

  DOI：10.1021/ol401152w

  日期：2013.6.7

  A facile one-pot synthetic route for preparing the novel benzofused tricyclic skeleton of 1,2,2a,8b-tetrahydrocyclobuta[a]naphthalenes 5 is developed. The route was realized by a NaH-mediated tandem aldol condensation/olefin migration/electrocyclization of o-allylbenzaldehydes 1 with cinnamyl sulfones 3 in good yields.

  开发了一种容易的一锅合成路线，以制备新型的1,2,2a，8b-四氢环丁[ a ]萘5苯并稠合的三环骨架。该途径是通过NaH介导的串联羟醛缩合/烯烃迁移/邻烯丙基甲醛1与肉桂基砜3的电环化以高收率实现的。
• Homoallylic alcohols from samarium diiodide-mediated coupling of allylic sulfones with carbonyl compounds
  作者：Jonathan Clayden、Marc Julia

  DOI：10.1039/c39940002261

  日期：——

  Reduction of allylic sulfones with samarium diiodide gives allylsamarium species which react in situ with carbonyl compounds, yielding homoallylic alcohols.

  三碘化二钐还原烯丙基砜生成烯丙基钐物种，该物种可原地与羰基化合物反应，生成高烯丙醇。
• One-pot synthesis of multisubstituted quaterphenyls and cyclopropanes
  作者：Meng-Yang Chang、Chieh-Kai Chan、Shin-Ying Lin、Ming-Hao Wu

  DOI：10.1016/j.tet.2013.09.060

  日期：2013.11

  quaterphenyls 3 or cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a regioselective [3C+3C] or [1C+2C] annulation. The reaction features mild conditions, multisubstitution, and functional groups tolerance and is transition metal catalyst-free. The protocol provides a novel alternative to the conventional methodologies for the synthesis of quaterphenyls or

  朝向多官能化quaterphenyls一种有效的一步合成路线3或环丙烷4选自取代的查耳酮开发1和砜2以良好的收率通过区域选择性[3C + 3C]或[1C + 2C]环。该反应具有温和的条件，多取代和对官能团的耐受性，并且不含过渡金属催化剂。该方案为合成四苯基或环丙烷的常规方法提供了一种新颖的替代方法。
• Palladium(II)-Catalyzed Acetoxylation and Chlorination of 2-Alkenyl<i>p</i>-Tolyl Sulfones
  作者：Katsuyuki Ogura、Nobuhiro Shibuya、Kazumasa Takahashi、Hirotada Iida

  DOI：10.1246/bcsj.57.1092

  日期：1984.4

  2-Alkenyl p-tolyl sulfones were converted into the corresponding 3-acetoxy(or chloro)-1-alkenyl p-tolyl sulfones via π-allylpalladium complexes which reacted regiospecifically with a nucleophile such as acetate anion or chloride anion in the presence of Cu(II).

  2-烯基对甲苯基砜通过 π-烯丙基钯配合物转化为相应的 3-乙酰氧基（或氯）-1-烯基对甲苯基砜，该配合物在 Cu 存在下与乙酸根阴离子或氯阴离子等亲核试剂发生区域特异性反应（二）。
• Allylic sulfones as allyl anion equivalents: homoallylic alcohols from metal catalysed reactions of sulfones with aldehydes and ketones
  作者：Jonathan Clayden、Marc Julia

  DOI：10.1039/c39940001905

  日期：——

  Reduction of allylic sulfones with diethylzinc, catalysed by palladium(0), gives nucleophilic organometallic species, which react in situ with carbonyl compounds to give homoallylic alcohols in high yield.

  在钯（0）的催化下，用二乙基锌还原烯丙基砜可得到亲核有机金属物质，该物质可与羰基化合物原位反应，从而以高收率得到均烯丙基醇。