1-(2-bromo-4,5-dimethoxybenzenesulfonyl)-2,5-dihydro-1H-pyrrole | 830319-62-5

• 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-(2-bromo-4,5-dimethoxybenzenesulfonyl)-2,5-dihydro-1H-pyrrole
• 英文别名: 1-((2-bromo-4,5-dimethoxyphenyl)sulfonyl)dihydropyrrole；1H-Pyrrole, 1-[(2-bromo-4,5-dimethoxyphenyl)sulfonyl]-2,5-dihydro-；1-(2-bromo-4,5-dimethoxyphenyl)sulfonyl-2,5-dihydropyrrole
• CAS: 830319-62-5
• 化学式: C₁₂H₁₄BrNO₄S
• 分子量: 348.217
• InChiKey: BRWXCOWUSLIKNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-4,5-dimethoxybenzenesulfonyl)-2,5-dihydro-1H-pyrrole 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以76%的产率得到4,5-dimethoxy-8-thia-9-azatricyclo[7.2.1.0^2,7]dodeca-2(7),3,5,10-tetraene-8,8-dioxide
  参考文献：
  名称：

  苯并环化双环 sultam 的非对映选择性功能化：在顺式 2,4-二芳基吡咯烷合成中的应用。

  摘要：

  描述了不饱和双环桥头化合物 5a 和 5b 的顺式二溴化，以及旨在了解这些反应的顺式立体化学结果的实验​​。在 5b 的情况下，随着 18b 的形成，发生了一种新型的溶剂依赖性碳正离子重排。顺式二溴化物 13a 和 13b 经历区域选择性脱溴化氢，并且描述了所得乙烯基溴化物 24a 在锂化和 Pd 偶联化学中的参与。在后者的情况下，苯乙烯基产物的氢化提供单一的非对映异构体。然后在溶解的金属还原条件下研究这些化合物，其中 NS 和 CS 键均发生断裂以提供顺式-2,4-二芳基取代的吡咯烷 35-37。

  DOI：

  10.3762/bjoc.5.69
• 作为产物：
  描述：

  4-溴黎芦醚 在 氯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.58h， 生成 1-(2-bromo-4,5-dimethoxybenzenesulfonyl)-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines

  摘要：

  The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.

  DOI：

  10.1021/ol0480123

文献信息

• A ring closing metathesis-manganese dioxide oxidation sequence for the synthesis of substituted pyrroles
  作者：Aaron Keeley、Shane McCauley、Paul Evans

  DOI：10.1016/j.tet.2016.03.088

  日期：2016.5

  The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were obtained for a variety of substituents and the procedure may also be conducted in one-pot. 2-Bromo N-sulfonyl adducts prepared in this manner were subjected to an intramolecular Heck-type cyclisation, forming cyclic sulfonamides.

  描述了闭环或烯炔复分解与氧化的组合以制备N-磺酰基吡咯。对于各种取代基均获得了合理的高收率，该方法也可以一锅进行。将以此方式制备的2-溴N-磺酰基加合物进行分子内Heck型环化，形成环状磺酰胺。
• Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of <i>cis</i>-2,4-diarylpyrrolidines
  作者：Susan Kelleher、Pierre-Yves Quesne、Paul Evans

  DOI：10.3762/bjoc.5.69

  日期：——

  The cis-dibromination of unsaturated bicyclic bridgehead sultams 5a and 5b, and experiments designed to understand the cis-stereochemical outcome of these reactions, are described. In the case of 5b, a novel solvent dependent carbocation rearrangement occurs with the formation of 18b. cis-Dibromides 13a and 13b undergo regioselective dehydrobromination, and the participation of the resultant vinyl

  描述了不饱和双环桥头化合物 5a 和 5b 的顺式二溴化，以及旨在了解这些反应的顺式立体化学结果的实验​​。在 5b 的情况下，随着 18b 的形成，发生了一种新型的溶剂依赖性碳正离子重排。顺式二溴化物 13a 和 13b 经历区域选择性脱溴化氢，并且描述了所得乙烯基溴化物 24a 在锂化和 Pd 偶联化学中的参与。在后者的情况下，苯乙烯基产物的氢化提供单一的非对映异构体。然后在溶解的金属还原条件下研究这些化合物，其中 NS 和 CS 键均发生断裂以提供顺式-2,4-二芳基取代的吡咯烷 35-37。
• An Investigation into the One-Pot Heck Olefination−Hydrogenation Reaction
  作者：Kimberly Geoghegan、Susan Kelleher、Paul Evans

  DOI：10.1021/jo200023r

  日期：2011.4.1

  Herein is described an operationally simple process concerning the observation that, following either inter-, or intramolecular Heck olefination, stirring of the so formed substituted alkenyl product under an atmosphere of hydrogen efficiently effects alkene hydrogenation. Overall this two-operation, one-pot "reductive Heck" sequence is notable since direct reductive Heck processes, using additives such as formate salts, are restricted to a limited range of substrates. In total 25 examples are reported (yields ranging from 0 to 95%), which were selected in order to probe the scope and limitations of this method. Finally, the utility of this sequence was demonstrated in a short synthesis of the calcimimetic agent, cinacalcet.
• Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines
  作者：Paul Evans、Thomas McCabe、Ben S. Morgan、Sophie Reau

  DOI：10.1021/ol0480123

  日期：2005.1.1

  The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.
• Ammonium formate-based one-pot reductive Heck reactions for the construction of cyclic sulfonamides
  作者：Aisha Khalifa、Lorna Conway、Kimberly Geoghegan、Paul Evans

  DOI：10.1016/j.tetlet.2017.10.053

  日期：2017.11

  A modified method is reported for the conversion of unsaturated sulfonamides into their cyclic saturated counterparts. This method utilises a single palladium catalyst for an intramolecular Heck reaction and subsequent transfer hydrogenation, which is achieved in one-pot following the addition of ammonium formate. Accordingly, a range of fourteen structural variations are reported and under optimal

  报道了一种改进的方法，用于将不饱和磺酰胺转化为其环状饱和对应物。该方法利用一种单一的钯催化剂进行分子内Heck反应和随后的转移氢化，这是在添加甲酸铵后一锅内完成的。因此，报道了十四种结构变化的范围，并且在最佳条件下以通常良好至优异的产率生成加合物。值得注意的是，在化合物28和29的情况下，可以实现对差异取代的二烯的区分，并且仅观察到该过程在空间上受阻更大的前体32下失败。