tert-butyl [2-formyl-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-4-yl]carbamate | 1159569-69-3

• 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: tert-butyl [2-formyl-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-4-yl]carbamate
• 英文别名: tert-butyl N-[5-formyl-2-methoxy-4-[2,3,4-trimethoxy-6-(triethylsilyloxymethyl)phenyl]phenyl]carbamate
• CAS: 1159569-69-3
• 化学式: C₂₉H₄₃NO₈Si
• 分子量: 561.748
• InChiKey: IIGNBAFVKVHWIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl [2-formyl-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-4-yl]carbamate 、 烯丙基溴化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以66%的产率得到tert-butyl [2-(1-hydroxybut-3-en-1-yl)-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-4-yl]carbamate
  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-hydroxymethyl-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-4-yl]carbamate 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到tert-butyl [2-formyl-2',3',4',5-tetramethoxy-6'-(triethylsilyloxymethyl)biphenyl-4-yl]carbamate
  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

文献信息

• Synthetic Approaches to Amino Analogues of <i>N</i>-Acetylcolchinol
  作者：Virginie Colombel、Olivier Baudoin

  DOI：10.1021/jo900632a

  日期：2009.6.5

  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.