ethyl 1-[(2,2-dimethylpropanoyl)amino]naphthalene-2-carboxylate | 1619257-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-[(2,2-dimethylpropanoyl)amino]naphthalene-2-carboxylate
• CAS: 1619257-83-8
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: HXHISFPYJOKSHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-[(2,2-dimethylpropanoyl)amino]naphthalene-2-carboxylate 在 ammonium carbonate 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 palladium diacetate 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 丙酮 、 乙腈 为溶剂， 反应 42.33h， 生成 3-(4-methoxybenzyl)-6-(morpholin-4-yl)benzo[h]quinazolin-4(3H)-one
  参考文献：
  名称：

  Substituted benzoquinazolinones. Part 1: Synthesis of 6-aminobenzo[h]quinazolinones via Buchwald–Hartwig amination from 6-bromobenzo[h]quinazolinones

  摘要：

  6-(Morpholin-4-yl)benzothlquinazolin-4(3H)-one derivatives 18a,b were prepared under Buchwald-Hartwig conditions by reacting 6-bromobenzo[h]quinazolin-4(3H)-ones 13a,b with morpholine in the presence of a Pd(OAc)(2)/XantPhos system in 1,4-dioxane as solvent. The starting 6-bromobenzo[h] quinazolin-4(3H)-ones 13 were synthesized via condensation of the ethyl 1-amino-4-bromonaphthalene-2-carboxylate (11) with formamide (Niementowski reaction), and then reaction of the obtained benzoquinazolinone 9 with appropriates benzyl bromides. Compound 11 was prepared using a three-step procedure involving (a) metalation of the N-Boc- or N-Piv-protected 1-aminonaphthalenes with t-BuLi, followed by reaction with ethyl chloroformate, (b) bromination of the naphthalene ring of ester 3 using NBS, and next (c) deprotecion of the amine group with TFA or HCI. Biological screening of the potential cytotoxicity of compounds 8, 9, 18b on A549 and HT29 cell lines, as well as on the lymphocytes showed that compound 18b has interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays were reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.117
• 作为产物：
  描述：

  1-naphthyl-N-pivalamide 、 氯甲酸乙酯 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 4.0h， 以32%的产率得到ethyl 1-[(2,2-dimethylpropanoyl)amino]naphthalene-2-carboxylate
  参考文献：
  名称：

  Substituted benzoquinazolinones. Part 1: Synthesis of 6-aminobenzo[h]quinazolinones via Buchwald–Hartwig amination from 6-bromobenzo[h]quinazolinones

  摘要：

  6-(Morpholin-4-yl)benzothlquinazolin-4(3H)-one derivatives 18a,b were prepared under Buchwald-Hartwig conditions by reacting 6-bromobenzo[h]quinazolin-4(3H)-ones 13a,b with morpholine in the presence of a Pd(OAc)(2)/XantPhos system in 1,4-dioxane as solvent. The starting 6-bromobenzo[h] quinazolin-4(3H)-ones 13 were synthesized via condensation of the ethyl 1-amino-4-bromonaphthalene-2-carboxylate (11) with formamide (Niementowski reaction), and then reaction of the obtained benzoquinazolinone 9 with appropriates benzyl bromides. Compound 11 was prepared using a three-step procedure involving (a) metalation of the N-Boc- or N-Piv-protected 1-aminonaphthalenes with t-BuLi, followed by reaction with ethyl chloroformate, (b) bromination of the naphthalene ring of ester 3 using NBS, and next (c) deprotecion of the amine group with TFA or HCI. Biological screening of the potential cytotoxicity of compounds 8, 9, 18b on A549 and HT29 cell lines, as well as on the lymphocytes showed that compound 18b has interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays were reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.117