(R)-4-(2,4-Dimethoxy-phenyl)-N-methoxy-2-triisopropylsilanyloxy-butyramide | 717099-08-6

• 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: (R)-4-(2,4-Dimethoxy-phenyl)-N-methoxy-2-triisopropylsilanyloxy-butyramide
• 英文别名: (2R)-4-(2,4-dimethoxyphenyl)-N-methoxy-2-tri(propan-2-yl)silyloxybutanamide
• CAS: 717099-08-6
• 化学式: C₂₂H₃₉NO₅Si
• 分子量: 425.641
• InChiKey: QGVIBKHRCSPXPB-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-(2,4-Dimethoxy-phenyl)-N-methoxy-2-triisopropylsilanyloxy-butyramide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3R,6S)-1,7-Dimethoxy-3-triisopropylsilanyloxy-1-aza-spiro[5.5]undeca-7,10-diene-2,9-dione 、 (3R,6R)-1,7-Dimethoxy-3-triisopropylsilanyloxy-1-aza-spiro[5.5]undeca-7,10-diene-2,9-dione
  参考文献：
  名称：

  Stereoselective nitrenium ion cyclizations: asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of fasicularin

  摘要：

  The asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of the marine natural product fasicularin is reported. The keystone of this divergent synthesis is the diastereoselective azaspirocyclization of an N-methoxy-gamma-arylbutanoamide, which is believed to proceed through the intermediacy of an N-acylnitrenium ion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.028
• 作为产物：
  描述：

  2,4-二甲氧基碘苯 在 palladium dichloride 咪唑 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 copper(l) iodide 、 硫酸 、 三苯基膦 作用下， 以 三乙胺 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 75.5h， 生成 (R)-4-(2,4-Dimethoxy-phenyl)-N-methoxy-2-triisopropylsilanyloxy-butyramide
  参考文献：
  名称：

  Stereoselective nitrenium ion cyclizations: asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of fasicularin

  摘要：

  The asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of the marine natural product fasicularin is reported. The keystone of this divergent synthesis is the diastereoselective azaspirocyclization of an N-methoxy-gamma-arylbutanoamide, which is believed to proceed through the intermediacy of an N-acylnitrenium ion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.028

文献信息

• Stereoselective nitrenium ion cyclizations: asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of fasicularin
  作者：Duncan J. Wardrop、Wenming Zhang、Chad L. Landrie

  DOI：10.1016/j.tetlet.2004.04.028

  日期：2004.5

  The asymmetric synthesis of the (+)-Kishi lactam and an intermediate for the preparation of the marine natural product fasicularin is reported. The keystone of this divergent synthesis is the diastereoselective azaspirocyclization of an N-methoxy-gamma-arylbutanoamide, which is believed to proceed through the intermediacy of an N-acylnitrenium ion. (C) 2004 Elsevier Ltd. All rights reserved.