1-[2-N-(Boc)aminophenyl]-4-oxobutanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-N-(Boc)aminophenyl]-4-oxobutanal
• 英文别名: tert-butyl N-[2-(4-oxobutanoyl)phenyl]carbamate
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: WNXVTMLHQKDTAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-N-(Boc)aminophenyl]-4-oxobutanal 在 甲酸铵 、 sodium acetate 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 以80%的产率得到2-[2-N-(Boc)aminophenyl]-1H-pyrrole
  参考文献：
  名称：

  Aminophenylpyrrole Synthesis and Application to Pyrrolo[1,2-c]quinazolinone Synthesis

  摘要：

  Aminophenylpyrroles have been synthesized by a three-step route from methyl N-(Boc)anthranilate (2). Amine protection of commercially available methyl anthranilate (1) gave Boc-protected methyl ester 2, which reacted with vinylmagnesium bromide in the presence of a catalytic amount of copper (I) cyanide to yield 1-[2-N-(Boc)aminophenyl]pent-4-en-1-one (3) in 43% yield. Oxidation of homoallylic ketone 3 using either a mixture of OsO4 center dot NaIO4 and 2,6-lutidine, or PdCl2-CuCl under oxygen atmosphere gave respectively aldehyde 4 and ketone 5. Treatment of 1,4-dicarbonyl compounds 4 and 5 with ammonium formate as well as primary amines under Paal-Knorr conditions afforded a set of eight 2-[2-N-(Boc)aminophenyl]pyrroles 6a-d and 7a-d. In addition, treatment of 2-[2-N-(Boc)aminophenyl]-1H-pyrrole 6a with NaH provided a novel entry to pyrrolo [1,2-c]quinazolin-5(6H)-one 8.

  DOI：

  10.3987/com-13-s(s)73
• 作为产物：
  描述：

  1-[2-N-(Boc)aminophenyl]pent-4-en-1-one 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以76%的产率得到1-[2-N-(Boc)aminophenyl]-4-oxobutanal
  参考文献：
  名称：

  Aminophenylpyrrole Synthesis and Application to Pyrrolo[1,2-c]quinazolinone Synthesis

  摘要：

  Aminophenylpyrroles have been synthesized by a three-step route from methyl N-(Boc)anthranilate (2). Amine protection of commercially available methyl anthranilate (1) gave Boc-protected methyl ester 2, which reacted with vinylmagnesium bromide in the presence of a catalytic amount of copper (I) cyanide to yield 1-[2-N-(Boc)aminophenyl]pent-4-en-1-one (3) in 43% yield. Oxidation of homoallylic ketone 3 using either a mixture of OsO4 center dot NaIO4 and 2,6-lutidine, or PdCl2-CuCl under oxygen atmosphere gave respectively aldehyde 4 and ketone 5. Treatment of 1,4-dicarbonyl compounds 4 and 5 with ammonium formate as well as primary amines under Paal-Knorr conditions afforded a set of eight 2-[2-N-(Boc)aminophenyl]pyrroles 6a-d and 7a-d. In addition, treatment of 2-[2-N-(Boc)aminophenyl]-1H-pyrrole 6a with NaH provided a novel entry to pyrrolo [1,2-c]quinazolin-5(6H)-one 8.

  DOI：

  10.3987/com-13-s(s)73

文献信息

• Compounds and Method for Treating Dyslipidemia
  申请人：Chen Xinchao

  公开号：US20070244095A1

  公开（公告）日：2007-10-18

  Compounds of formula I wherein n, m, p, q, Y, R 1 R 2 , R 3a , R 3b , R 4 , R 5 , and R 6 are as defined herein and their pharmaceutical compositions and methods of use are disclosed.

  公式I的化合物，其中n，m，p，q，Y，R1R2，R3a，R3b，R4，R5和R6的定义如本文所述，并公开了它们的药物组合物和使用方法。
• Compounds and Methods for Treating Dyslipidemia
  申请人：Chen Xinchao

  公开号：US20100204207A1

  公开（公告）日：2010-08-12

  Compounds of Formula (I): wherein n, m, p, q, Y, R1, R2, R3a, R3b, R4, R5, and R6 are as defined herein and their pharmaceutical compositions and methods of use are disclosed.

  本发明涉及公式（I）的化合物，其中n，m，p，q，Y，R1，R2，R3a，R3b，R4，R5和R6如本文所定义，并公开了它们的制药组合物和使用方法。
• US7786108B2
  申请人：——

  公开号：US7786108B2

  公开（公告）日：2010-08-31
• Aminophenylpyrrole Synthesis and Application to Pyrrolo[1,2-c]quinazolinone Synthesis
  作者：William D. Lubell、Aurélie A. Dörr

  DOI：10.3987/com-13-s(s)73

  日期：——

  Aminophenylpyrroles have been synthesized by a three-step route from methyl N-(Boc)anthranilate (2). Amine protection of commercially available methyl anthranilate (1) gave Boc-protected methyl ester 2, which reacted with vinylmagnesium bromide in the presence of a catalytic amount of copper (I) cyanide to yield 1-[2-N-(Boc)aminophenyl]pent-4-en-1-one (3) in 43% yield. Oxidation of homoallylic ketone 3 using either a mixture of OsO4 center dot NaIO4 and 2,6-lutidine, or PdCl2-CuCl under oxygen atmosphere gave respectively aldehyde 4 and ketone 5. Treatment of 1,4-dicarbonyl compounds 4 and 5 with ammonium formate as well as primary amines under Paal-Knorr conditions afforded a set of eight 2-[2-N-(Boc)aminophenyl]pyrroles 6a-d and 7a-d. In addition, treatment of 2-[2-N-(Boc)aminophenyl]-1H-pyrrole 6a with NaH provided a novel entry to pyrrolo [1,2-c]quinazolin-5(6H)-one 8.