methyl 2-{[N-(2-bromo-5-methoxybenzyl)-2'-(trimethylsilyl)ethylsulfonamido](phenyl)methyl}acrylate | 915777-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 2-{[N-(2-bromo-5-methoxybenzyl)-2'-(trimethylsilyl)ethylsulfonamido](phenyl)methyl}acrylate
• 英文别名: methyl 2-((N-2-bromo-5-methoxy-benzyl-2-(trimethylsilyl)ethan-3-ylsulfonamido)(phenyl)methyl)acrylate；Methyl 2-[[(2-bromo-5-methoxyphenyl)methyl-(2-trimethylsilylethylsulfonyl)amino]-phenylmethyl]prop-2-enoate；methyl 2-[[(2-bromo-5-methoxyphenyl)methyl-(2-trimethylsilylethylsulfonyl)amino]-phenylmethyl]prop-2-enoate
• CAS: 915777-59-2
• 化学式: C₂₄H₃₂BrNO₅SSi
• 分子量: 554.577
• InChiKey: UAIRTESMEBERAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-{[N-(2-bromo-5-methoxybenzyl)-2'-(trimethylsilyl)ethylsulfonamido](phenyl)methyl}acrylate 在 palladium diacetate 、 poly(ethylene glycol) 3400 、 potassium carbonate 作用下， 反应 0.5h， 以83%的产率得到methyl 8-methoxy-3-phenyl-2-[2-(trimethylsilyl)ethylsulfonyl]-2,3-dihydro-1H-benzo[c]azepine-4-carboxylate
  参考文献：
  名称：

  用于合成苯并氮杂的聚乙二醇中的微波辅助 Heck 反应

  摘要：

  烷基化 2-（三甲基甲硅烷基）乙磺酰基 (SES) 保护的 β-氨基酯的 Heck 反应以良好的产率提供苯并氮杂。当反应以 PEG 3400 作为溶剂在微波活化下进行时，获得了良好的环化选择性。用 HF 裂解 SES 基团提供相应的游离苯并氮杂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600680
• 作为产物：
  描述：

  2-(三甲基硅基)乙磺酰胺 在 三乙烯二胺 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 methyl 2-{[N-(2-bromo-5-methoxybenzyl)-2'-(trimethylsilyl)ethylsulfonamido](phenyl)methyl}acrylate
  参考文献：
  名称：

  Synthesis of novel poly(ethylene glycol) supported benzazepines: the crucial role of PEG on the selectivity of an intramolecular Heck reaction

  摘要：

  Poly(ethylene glycol) (PEG 3400) was used as a soluble polymeric support for the synthesis of a series of novel benzazepines. The key step for the preparation of these heterocycles was a phosphine-free palladium-catalyzed Heck reaction. Palladium nanoparticles formed during the course of the reaction were characterized. The presence of PEG 3400 influenced the outcome of the reaction in terms of selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.009

文献信息

• A Microwave-Assisted Heck Reaction in Poly(ethylene glycol) for the Synthesis of Benzazepines
  作者：Valérie Declerck、Patrice Ribière、Yannig Nédellec、Hassan Allouchi、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/ejoc.200600680

  日期：2007.1

  The Heck reaction of alkylated 2-(trimethylsilyl)ethanesulfonyl (SES)-protected β-amino esters provides benzazepines in good yields. Good selectivity towards cyclisation was obtained when the reaction was performed in PEG 3400 as the solvent under microwave activation. Cleavage of the SES group with HF provides the corresponding free benzazepine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  烷基化 2-（三甲基甲硅烷基）乙磺酰基 (SES) 保护的 β-氨基酯的 Heck 反应以良好的产率提供苯并氮杂。当反应以 PEG 3400 作为溶剂在微波活化下进行时，获得了良好的环化选择性。用 HF 裂解 SES 基团提供相应的游离苯并氮杂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of novel poly(ethylene glycol) supported benzazepines: the crucial role of PEG on the selectivity of an intramolecular Heck reaction
  作者：Patrice Ribière、Valérie Declerck、Yannig Nédellec、Neerja Yadav-Bhatnagar、Jean Martinez、Frédéric Lamaty

  DOI：10.1016/j.tet.2006.08.009

  日期：2006.10

  Poly(ethylene glycol) (PEG 3400) was used as a soluble polymeric support for the synthesis of a series of novel benzazepines. The key step for the preparation of these heterocycles was a phosphine-free palladium-catalyzed Heck reaction. Palladium nanoparticles formed during the course of the reaction were characterized. The presence of PEG 3400 influenced the outcome of the reaction in terms of selectivity. (c) 2006 Elsevier Ltd. All rights reserved.