tert-butyl N-(5-formyl-2-methoxyphenyl)carbamate | 1159569-64-8

• 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 N-(5-formyl-2-methoxyphenyl)carbamate
• CAS: 1159569-64-8
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: LTHLHPKCXCKIHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(5-formyl-2-methoxyphenyl)carbamate 、 甲基溴化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以79%的产率得到tert-butyl [5-(1-hydroxyethyl)-2-methoxyphenyl]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 [5-(hydroxymethyl)-2-methoxyphenyl]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 6.0h， 以96%的产率得到tert-butyl N-(5-formyl-2-methoxyphenyl)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

• 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：EP2928869B1

  公开（公告）日：2019-02-20
• 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.