1-[4-(tert-butoxycarbonylamino)-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-2-yl]ethyl 4-nitrobenzoate | 1159817-80-7

• 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-[4-(tert-butoxycarbonylamino)-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-2-yl]ethyl 4-nitrobenzoate
• CAS: 1159817-80-7
• 化学式: C₃₇H₅₀N₂O₁₁Si
• 分子量: 726.896
• InChiKey: UJNVLTFGIAFTIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.08
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  153.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-[4-(tert-butoxycarbonylamino)-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-2-yl]ethyl 4-nitrobenzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 以53%的产率得到1-[4-(tert-butoxycarbonylamino)-6'-hydroxymethyl-2',3',4',5-tetramethoxybiphenyl-2-yl]ethyl 4-nitrobenzoate
  参考文献：
  名称：

  Synthetic Approaches to Amino Analogues of N-Acetylcolchinol

  摘要：

  A straightforward synthesis of aminodibenzoxepines, new analogues of N-acetyleolchinol, is reported by using two different strategies. The first strategy involves a Grignard addition, a biaryl Suzuki-Miyaura coupling, and a HF-mediated cyclodehydration as key steps. A second strategy, better adapted to the synthesis of analogues bearing a benzylic substituent, was designed by inverting the order of the Grignard addition and the biaryl coupling. This allowed the rapid and reliable production of a series of substituted aminodibenzoxepines. A chelate model was proposed to account for the diastereoselectivity observed in the Grignard addition step.

  DOI：

  10.1021/jo900632a
• 作为产物：
  描述：

  tert-butyl [2-(1-hydroxyethyl)-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-4-yl]carbamate 、 4-硝基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到1-[4-(tert-butoxycarbonylamino)-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-2-yl]ethyl 4-nitrobenzoate
  参考文献：
  名称：

  Synthetic Approaches to Amino Analogues of N-Acetylcolchinol

  摘要：

  A straightforward synthesis of aminodibenzoxepines, new analogues of N-acetyleolchinol, is reported by using two different strategies. The first strategy involves a Grignard addition, a biaryl Suzuki-Miyaura coupling, and a HF-mediated cyclodehydration as key steps. A second strategy, better adapted to the synthesis of analogues bearing a benzylic substituent, was designed by inverting the order of the Grignard addition and the biaryl coupling. This allowed the rapid and reliable production of a series of substituted aminodibenzoxepines. A chelate model was proposed to account for the diastereoselectivity observed in the Grignard addition step.

  DOI：

  10.1021/jo900632a