E-3-溴-1-(对甲苯磺酰基)丙烯 | 28187-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: E-3-溴-1-(对甲苯磺酰基)丙烯
• 英文名称: (E)-3-bromo-1-tosyl-1-propene
• 英文别名: E-3-bromo-1-(p-tolylsulfonyl)propene；(E)-1-((3-bromoprop-1-en-1-yl)sulfonyl)-4-methylbenzene；(E)-[(3-bromoprop-1-en-1-yl)sulfonyl]-4-methylbenzene；trans-3-Bromprop-1-enyl-p-tolylsulfon；(3-bromo-trans-propenyl)-p-tolyl sulfone；(3-Brom-trans-propenyl)-p-tolyl-sulfon；3-Brom-1-p-toluolsulfonyl-propen-(1)；1-[(1E)-3-Bromoprop-1-ene-1-sulfonyl]-4-methylbenzene；1-[(E)-3-bromoprop-1-enyl]sulfonyl-4-methylbenzene
• CAS: 28187-88-4
• 化学式: C₁₀H₁₁BrO₂S
• 分子量: 275.166
• InChiKey: QZORILSDLSFDSR-KRXBUXKQSA-N

物化性质

• 沸点：
  405.9±45.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

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：
  0.2
• 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：

  E-3-溴-1-(对甲苯磺酰基)丙烯 在 sodium nitrite 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以87%的产率得到(E)-3-(p-toluenesulfonyl)-2-propene-1-ol
  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：

  (E)-3-(p-toluenesulfonyl)-2-propene-1-ol 在 吡啶 、 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到E-3-溴-1-(对甲苯磺酰基)丙烯
  参考文献：
  名称：

  “Syn-Effect” in the Conversion of (E)-Vinylic Sulfones to the Corresponding Allylic Sulfones

  摘要：

  研究发现，在温和条件下通过碱性处理，(E)-乙烯基砜类化合物倾向于优先形成动力学控制的(Z)-烯丙基砜类产物，而(Z)-乙烯基砜则生成(E)-烯丙基砜。这种立体化学关系可通过“邻位效应”来解释，并且通过观察相应的γ-单取代或γ,γ-双取代乙烯基砜所生成的烯丙基砜的E/Z比率，确定了不同取代基的相对程度如下：RO–（R=CH3, C2H5）＞ ArO–（Ar=p-CH3OC6H4, p-CH3C6H4, C6H5, p-NO2C6H4）≥ AcO–＞ Cl– ≥ Br–＞ CH3–＞ CH3S– ≥ –CH2–（环状和非环状）＞(CH3)2CH–>＞(CH3)3C–, C6H5–。对一些乙烯基砜进行了X射线晶体学分析，以揭示“邻位效应”的起源。

  DOI：

  10.1246/bcsj.65.75

文献信息

• Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides
  作者：Niall Collins、Robert Connon、Goar Sánchez‐Sanz、Paul Evans

  DOI：10.1002/ejoc.202001065

  日期：2020.10.22

  The efficient isomerisation of a range of γ‐azido substituted vinyl sulfones is reported. The corresponding vinyl azides are typically obtained with high levels of Z‐stereochemistry. An exception is when R is an α‐methyl substituent is present when the E‐vinyl azide was preferred.

  据报道，一系列γ-叠氮基取代的乙烯基砜得到了有效的异构化。相应的乙烯基叠氮化物通常以较高的Z立体化学含量获得。一个例外是，当优先使用E-乙烯基叠氮化物时，当R是一个α-甲基取代基时。
• One-Pot Allylation–Intramolecular Vinylogous Michael Addition–Isomerization Cascade of <i>o</i>-Hydroxycinnamates and Congeners: Synthesis of Substituted Benzofuran Derivatives
  作者：Battu Harish、Manyam Subbireddy、Owk Obulesu、Surisetti Suresh

  DOI：10.1021/acs.orglett.9b00414

  日期：2019.3.15

  intramolecular vinylogous Michael addition leading to the synthesis of heterocycles has been disclosed. Base-promoted one-pot sequential O-allylation of o-hydroxy-cinnamates or -cinnamonitrile or -chalcones with γ-bromocrotonates followed by an intramolecular conjugate addition of vinylogous Michael donors resulted in the formation of highly substituted benzofuran derivatives in good to excellent yields. The intramolecular

  已经公开了导致杂环的合成的独特的分子内乙烯基乙烯基迈克尔加成。碱促进的邻位羟基肉桂酸酯或-肉桂腈或-邻苯二甲酸酯与γ-溴丁酸的一锅顺序O-烯丙基化反应，然后在分子内共轭添加乙烯基Michael供体导致高取代度的高取代苯并呋喃衍生物形成。分子内事件继之以两个[1,3] -H转变导致芳构化，似乎是这种前所未有的转化成功的关键。
• Facile synthesis of substituted diaryl sulfones <i>via</i> a [3 + 3] benzannulation strategy
  作者：Xiang-zheng Tang、Lang Tong、Hua-ju Liang、Jie Liang、Yong Zou、Xue-jing Zhang、Ming Yan、Albert S. C. Chan

  DOI：10.1039/c8ob00662h

  日期：——

  base-mediated [3 + 3] benzannulation strategy for the conversion of 1,3-bis(sulfonyl)propenes and β,γ-unsaturated α-ketoesters to diaryl sulfones has been developed. This method provides facile, metal-free and efficient access to highly substituted diaryl sulfones in good to excellent yields. In addition, the sulfonyl group could be easily removed or converted to other functional groups via an organostannane

  已开发出一种由碱介导的[3 + 3]苯环芳构化策略，可将1,3-双（磺酰基）丙烯和β，γ-不饱和α-酮酸酯转化为二芳基砜。该方法可以轻松，无金属且高效地获得高取代的二芳基砜，且收率良好。另外，磺酰基可通过有机锡烷中间体容易地除去或转化为其他官能团。
• A convenient synthesis of 2-substituted benzofurans from salicylaldehydes
  作者：Swetha Reddy、Srinivas Thadkapally、Mounika Mamidyala、Jagadeesh Babu Nanubolu、Rajeev S. Menon

  DOI：10.1039/c4ra14948c

  日期：——

  Base-mediated cyclocondensation of 2-hydroxybenzaldehydes with 3-bromo-1-(arylsulfonyl)propenes and 4-bromocrotonates afforded (E)-2-(2-sulfonylvinyl)benzofurans and (E)-2-benzofuranyl-3-acrylates respectively.

  2-羟基苯甲醛与3-溴-1-（芳基磺酰基）丙烯和4-溴巴豆酸酯的碱介导的环缩合分别得到（E）-2-（2-磺酰基乙烯基）苯并呋喃和（E）-2-苯并呋喃基-3-丙烯酸酯。
• Design and development of intramolecular doubly vinylogous Michael addition to access 3-aryl substituted 2-alkenyl-benzofurans and -indoles
  作者：Manyam Subbi Reddy、Jagadeesh Babu Nanubolu、Surisetti Suresh

  DOI：10.1039/d3ob00861d

  日期：——

  The first intramolecular doubly vinylogous Michael addition (DVMA) has been revealed for the construction of 2-alkenyl benzofuran and 2-alkenyl indole derivatives.

  首次揭示了分子内双乙烯基迈克尔加成（DVMA），用于构建 2-烯基苯并呋喃和 2-烯基吲哚衍生物。