1-(phenylsulfonyl)buta-1,2-diene | 55136-85-1

• 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-(phenylsulfonyl)buta-1,2-diene
• CAS: 55136-85-1
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: VMPCREWTLNPGIC-UHFFFAOYSA-N

物化性质

• 沸点：
  358.3±15.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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-(phenylsulfonyl)buta-1,2-diene 在 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.08h， 生成 2-丁炔基苯基砜
  参考文献：
  名称：

  Cycloaddition of (phenylsulfonyl)-1,2-propadienes with diazomethane. Novel rearrangement reactions of the resulting cycloadducts

  摘要：

  The cycloaddition reactions of several phenylsulfonyl-substituted allenes with diazomethane have been investigated. The major products formed were identified as 3-(phenylsulfonyl)-4-methylene-2-pyrazolines. These pyrazolines engage in a variety of mechanistically interesting transformations, ranging from base-catalyzed rearrangements to addition of Grignard reagents. The dipolar cycloadduct derived from the reaction of diazomethane with 3-(phenylsulfonyl)-1,2-butadiene undergoes a 1,3-phenylsulfonyl shift upon irradiation to give 3-methyl-4-[(phenylsulfonyl)methyl]pyrazole. The cycloadduct derived from there action of 2,3-bis(phenylsulfonyl)-1-propene with diazomethane readily loses nitrogen upon photolysis to give 1-[(phenylsulfonyl)methyl]-1-(phenylsulfonyl)cyclopropane. This cyclopropane affords a variety of novel rearranged structures when treated with several different bases. The products obtained can be rationalized in terms of a base-catalyzed rearrangement of the above cyclopropane to a-methyl(phenylsulfonyl)allene which reacts further with the particular base used to produce the observed products.

  DOI：

  10.1021/jo00060a021
• 作为产物：
  描述：

  but-3-yn-2-yl benzenesulfinate 在 silver hexafluoroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到1-(phenylsulfonyl)buta-1,2-diene
  参考文献：
  名称：

  亚磺酸盐作为路易斯碱有机催化剂的α取代的电子缺陷型烯的独特反应性

  摘要：

  突出了α-取代的烯基砜和烯丙基酯与迈克尔受体的高效亚磺酸盐催化的分子间加成反应。该序列在温和条件下进行，以提供可扩展且高效的通用功能性炔烃，在炔丙基位置显示四级立体中心。除了完善的膦和胺催化剂以外，这项工作还丰富了丙二烯化学领域的路易斯碱有机催化剂的多样性。

  DOI：

  10.1002/adsc.201600929

文献信息

• Unique Reactivity of α-Substituted Electron-Deficient Allenes using Sulfinate Salts as Lewis Base Organocatalysts
  作者：Thomas Martzel、Jean-François Lohier、Annie-Claude Gaumont、Jean-François Brière、Stéphane Perrio

  DOI：10.1002/adsc.201600929

  日期：2017.1.4

  efficient sulfinate‐catalyzed intermolecular addition reaction of α‐substituted allenyl sulfones and allenoates with Michael acceptors is highlighted. The sequence proceeds under mild conditions to provide a scalable and efficient access to versatile functionalized alkynes, displaying a quaternary stereocentre at the propargylic position. This work enriches the diversity of Lewis base organocatalysts

  突出了α-取代的烯基砜和烯丙基酯与迈克尔受体的高效亚磺酸盐催化的分子间加成反应。该序列在温和条件下进行，以提供可扩展且高效的通用功能性炔烃，在炔丙基位置显示四级立体中心。除了完善的膦和胺催化剂以外，这项工作还丰富了丙二烯化学领域的路易斯碱有机催化剂的多样性。
• The [2,3]-sigmatropic rearrangement of propargyl benzenesulphinates to allenyl phenyl sulphones
  作者：S. Braverman、H. Mechoulam

  DOI：10.1016/s0040-4020(01)97078-4

  日期：1974.1

  undergo thermal rearrangement in high yields to sulphones, accompanied by a simultaneous acetylene-allene isomerization. The allenic sulphones produced by the rearrangement of the α-monosubstituted propargyl esters underwent further rearrangement under the reaction conditions, to γ-substituted propargyl phenyl sulphones, by way of a base-catalyzed [1,3] - prototropic shift. A kinetic study of the rearrangement

  发现α-甲基-，α-苯基-，α-α-二甲基-和α-乙基-α-甲基炔丙基苯磺酸盐进行热重排成砜，同时发生乙炔-丙二烯异构化。通过α-单取代的炔丙基酯的重排而产生的烯丙砜在反应条件下通过碱催化的[1,3]-质变而进一步重排为γ-取代的炔丙基苯基砜。使用两种不同的酯进行了重排反应的动力学研究。这项研究表明，重排对溶剂电离能力和取代基的影响显示出相对较低的敏感性。这些数据和其他相关证据表明，一致的[2,3]-σ重排。
• Observation of the First Heck-Type Cross-Coupling Reaction of Allenes with Aryl Halides. Synthesis of Polysubstituted 1,2-Allenyl Sulfones
  作者：Chunling Fu、Shengming Ma

  DOI：10.1021/ol050301j

  日期：2005.4.14

  [reaction: see text] The Heck-type allenylation of aryl halides with allenes has been observed for the first time: The regioselectivity of intermolecular carbopalladation of 1,2-allenyl sulfones affording vinylic Pd intermediates is completely opposite to what was reported in the literature.

  [反应：见正文]首次观察到芳基卤化物与烯丙基的Heck型烯丙基化：提供乙烯基Pd中间体的1,2-烯基砜的分子间碳钯反应的区域选择性与文献报道完全相反。
• Highly Regio- and Stereoselective Oxidative Hydroacetoxylation of 1,2-Allenylic Sulfoxides via a Different Mechanism
  作者：Chao Zhou、Zhao Fang、Chunling Fu、Shengming Ma

  DOI：10.1021/jo802755k

  日期：2009.4.3

  A highly regio- and stereoselective oxidative hydroacetoxylation of 1,2-allenylic sulfoxides affording 1-sulfonyl-1-alken-3-yl acetates in moderate to good yields was developed. Through the X-ray diffraction study, it was observed that the reaction may proceed via a 5-membered cyclic intermediate and the −OAc attacks the chiral carbon atom, which is different from what was observed in our previous

  开发了1，2-烯丙基亚砜的高度区域和立体选择性氧化氢乙酰氧基化，以中等至良好的产率提供了1-磺酰基-1-链烯基-3-基乙酸酯。通过X射线衍射研究中，观察到反应可以经由5元环的环状中间体和继续- OAC攻击的手性碳原子，这是从在我们以前的研究中观察到的不同。
• Synthesis of 1,4-Enamino Ketones by [3,3]-Rearrangements of Dialkenylhydroxylamines
  作者：Wiktoria H. Pecak、Jongwoo Son、Amy J. Burnstine、Laura L. Anderson

  DOI：10.1021/ol501230e

  日期：2014.7.3

  4-enamino ketones has been achieved through the [3,3]-rearrangement of dialkenylhydroxylamines generated from the addition of N-alkenylnitrones to electron-deficient allenes. The mild conditions required for this reaction, and the simultaneous installation of a fluorenyl imine N-protecting group as a consequence of the rearrangement, avoid spontaneous cyclization of the 1,4-enamino ketones to form the

  1,4-烯氨基酮的合成是通过将N-烯基硝酮加到缺电子的烯中而生成的二烯基羟胺的[3,3]重排而实现的。该反应所需的温和条件以及由于重排而同时安装的芴基亚胺N-保护基团，避免了1,4-烯氨基酮的自发环化反应形成相应的吡咯，并允许分离和控制这些反应性中间体的不同功能化。讨论了该新方法的优化，范围和耐受性，并证明了该产品可用于合成吡咯，1,4-二酮和呋喃。