1-(2-bromo-4,5-dimethoxybenzenesulfonyl)-2,4,5,6,7,7a-hexahydro-1H-indole | 1218787-86-0

• 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)-2,4,5,6,7,7a-hexahydro-1H-indole
• 英文别名: 1-(2-Bromo-4,5-dimethoxyphenyl)sulfonyl-2,4,5,6,7,7a-hexahydroindole
• CAS: 1218787-86-0
• 化学式: C₁₆H₂₀BrNO₄S
• 分子量: 402.309
• InChiKey: GUBREIAZHUSRAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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)-2,4,5,6,7,7a-hexahydro-1H-indole 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以69%的产率得到1-((2-bromo-4,5-dimethoxyphenyl)sulfonyl)-4,5,6,7-tetrahydro-1H-indole
  参考文献：
  名称：

  闭环易位-二氧化锰氧化顺序合成取代吡咯

  摘要：

  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。

  DOI：

  10.1016/j.tet.2016.03.088
• 作为产物：
  描述：

  2-溴-4,5-二甲氧基苯磺酰氯 在 碘 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1-(2-bromo-4,5-dimethoxybenzenesulfonyl)-2,4,5,6,7,7a-hexahydro-1H-indole
  参考文献：
  名称：

  卤离子触发不饱和苯并双环和三环磺酰胺的重排

  摘要：

  ha离子介导的一系列苯并稠合的双环和三环磺酰胺的1,2-Wagner-Meerwein型重排。在这种重排过程中，迁移的碳-碳键被选择性地设置在起始材料的分子内Mizoroki-Heck（IHR）合成中。因此，该方法构成了访问在Mizoroki-Heck反应中未观察到的环状磺酰胺类区域异构体的方法。

  DOI：

  10.1021/jo401888f

文献信息

• 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。
• Selective generation of quaternary all-carbon-centres through Heck-cyclisations: synthesis of mesembrane
  作者：Johannes E. M. N. Klein、Kimberly Geoghegan、Nicolas Méral、Paul Evans

  DOI：10.1039/b923175g

  日期：——

  Described is an observation that the intramolecular Heck reaction of a trisubstituted alkene proceeds with high regioselectivity and leads to the preferential formation of a quaternary all-carbon-centre. This observation was subsequently applied in a short synthesis of (±)-mesembrane.

  描述了三取代烯烃的分子内 Heck 反应以高区域选择性进行并导致优先形成四元全碳中心的观察结果。这一观察结果随后被应用于(±)-膜的简短合成。
• 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.
• 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。
• Halonium Ion Triggered Rearrangement of Unsaturated Benzo-Annulated Bi- and Tricyclic Sulfonamides
  作者：Kimberly Geoghegan、Shaun Smullen、Paul Evans

  DOI：10.1021/jo401888f

  日期：2013.10.18

  The halonium ion mediated 1,2-Wagner–Meerwein-type rearrangement of a series of benzo-fused bi- and tricyclic sulfonamides is reported. During this rearrangement the carbon–carbon bond that migrates was selectively set in the intramolecular Mizoroki–Heck (IHR) synthesis of the starting materials. Consequently, this method constitutes a means to access the regioisomeric series of cyclic sulfonamides

  ha离子介导的一系列苯并稠合的双环和三环磺酰胺的1,2-Wagner-Meerwein型重排。在这种重排过程中，迁移的碳-碳键被选择性地设置在起始材料的分子内Mizoroki-Heck（IHR）合成中。因此，该方法构成了访问在Mizoroki-Heck反应中未观察到的环状磺酰胺类区域异构体的方法。