6-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde | 132279-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde
• 英文别名: 6-Bromo-4-hydroxy-1-methyl-2-oxoquinoline-3-carbaldehyde
• CAS: 132279-64-2
• 化学式: C₁₁H₈BrNO₃
• 分子量: 282.093
• InChiKey: JCVKZGVUUQXZKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde 、 N-乙酰甘氨酸 在 哌啶 、 乙酸酐 作用下， 反应 6.0h， 以88%的产率得到N-(9-Bromo-6-methyl-2,5-dioxo-5,6-dihydro-2H-pyrano[3,2-c]quinolin-3-yl)-acetamide
  参考文献：
  名称：

  Gupta, M.C.L.N.; Rao, V. Sudhakar; Darbarwar, Malleshwar, Synthetic Communications, 1990, vol. 20, # 14, p. 2103 - 2111

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-bromophenyl)-2-cyano-N-methylacetamide 、 N,N-二甲基甲酰胺 在 三氟甲磺酸酐 作用下， 反应 12.0h， 以68%的产率得到6-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde
  参考文献：
  名称：

  Triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides: a concise synthesis of glycocitlone alkaloids

  摘要：

  A method is presented for the concise synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones through triflic anhydride-mediated tandem formylation/cyclization of cyanoacetanilides. This tandem process was successfully used for the rapid syntheses of glycocitlones A and C. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.073

文献信息

• α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones
  作者：Yusuke Kobayashi、Terue Nakatani、Rie Tanaka、Mari Okada、Eri Torii、Takashi Harayama、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2011.03.040

  日期：2011.5

  The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.
• Gupta, M. C. L. N.; Darbarwar, Malleshwar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 11, p. 1080 - 1082
  作者：Gupta, M. C. L. N.、Darbarwar, Malleshwar

  DOI：——

  日期：——
• GUPTA, M. C. L. N.;RAO, V. SUDHAKAR;DARBARWAR, MALLESHWAR, SYNTH. COMMUN., 20,(1990) N4, C. 2103-2111
  作者：GUPTA, M. C. L. N.、RAO, V. SUDHAKAR、DARBARWAR, MALLESHWAR

  DOI：——

  日期：——