N-(2-bromo-5-methoxyphenyl)-N-(2-trimethylsilylethoxymethyl)cyclopentanecarboxamide | 1242077-78-6

• 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: N-(2-bromo-5-methoxyphenyl)-N-(2-trimethylsilylethoxymethyl)cyclopentanecarboxamide
• CAS: 1242077-78-6
• 化学式: C₁₉H₃₀BrNO₃Si
• 分子量: 428.442
• InChiKey: FMBCWVBKBWDDSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-bromo-5-methoxyphenyl)-N-(2-trimethylsilylethoxymethyl)cyclopentanecarboxamide 在 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 以77%的产率得到N-(3-methoxyphenyl)-N-(2-trimethylsilylethoxymethyl)cyclopentanecarboxamide
  参考文献：
  名称：

  Pd-Catalyzed Assembly of Spirooxindole Natural Products: A Short Synthesis of Horsfiline

  摘要：

  The Pd-catalyzed intramolecular alpha-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.

  DOI：

  10.1021/jo101401z
• 作为产物：
  描述：

  N-(2-bromo-5-methoxyphenyl)cyclopentanecarboxamide 、 2-(三甲基硅烷基)乙氧甲基氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以53%的产率得到N-(2-bromo-5-methoxyphenyl)-N-(2-trimethylsilylethoxymethyl)cyclopentanecarboxamide
  参考文献：
  名称：

  Pd-Catalyzed Assembly of Spirooxindole Natural Products: A Short Synthesis of Horsfiline

  摘要：

  The Pd-catalyzed intramolecular alpha-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.

  DOI：

  10.1021/jo101401z

文献信息

• Pd-Catalyzed Assembly of Spirooxindole Natural Products: A Short Synthesis of Horsfiline
  作者：Nina Deppermann、Heike Thomanek、Alexander H. G. P. Prenzel、Wolfgang Maison

  DOI：10.1021/jo101401z

  日期：2010.9.3

  The Pd-catalyzed intramolecular alpha-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.