(2-氧代-1H-喹啉-3-基)乙酸酯 | 26386-87-8

• 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
• 中文名称: (2-氧代-1H-喹啉-3-基)乙酸酯
• 英文名称: 3-acetoxy-2-quinolinone
• 英文别名: 3-(Acetyloxy)quinolin-2(1H)-one；2-oxo-1,2-dihydroquinolin-3-yl acetate；(2-oxo-1H-quinolin-3-yl) acetate
• CAS: 26386-87-8
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: UTIGEXXLPIATRW-UHFFFAOYSA-N

物化性质

• 沸点：
  432.4±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-氧代-1H-喹啉-3-基)乙酸酯 在 水 、 碘 、 sodium hydride 、 potassium carbonate 、 mercury(II) oxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 29.5h， 生成 5,7-Dihydro-5-methylcyclohexa<1>benzazocine-6,7-dione
  参考文献：
  名称：

  Photoinduced molecular transformations. 128. Regioselective [2 + 2] photocycloaddition of 3-acetoxyquinolin-2(1H)-one with alkenes and formation of furo[2,3-c]quinolin-4(5H)-ones, 1-benzazocine-2,3-diones, and cyclopropa[d]benz[1]azepine-2,3-diones via a .beta.-scission of cyclobutanoxyl radicals generated from the resulting [2 + 2] photoadducts

  摘要：

  We have found that [2 + 2]pi photoadducts can be obtained by the photoaddition of 3-acetoxyquinolin-2(1H)-one with acyclic and cyclic alkenes. The photoaddition of 3-acetoxy-2-quinolin-2(1H)-one with 2-methylpropene, 2,3-dimethyl-2-butene, and 2-methoxypropene thus afforded regioselective head-to-tail adducts in 59-97% yields. The photoaddition of 3-acetoxy-2-quinolin-2(1H)-one with cyclopentene and cyclohexene resulted in the formation of sterically disfavored cis-cisoid-cis photoadducts as the major products, with the accompanying formation of cis-transoid-cis photoadducts as the minor products in combined yields of 87 and 66%, respectively. The photolysis of the hypoiodites generated in situ from cyclobutanols derived from all of the photoadducts induced beta-scissions at the outer bonds of the corresponding cyclobutanoxyl radicals to give furo[2,3-c]quinolin-4(5H)-ones in 15-50% yields with an accompanying formation of 7- and 8-membered lactams arising from beta-scissions at the catacondensed bonds of the cyclobutanoxyl radicals in 2-62% yields. The molecular structure of one of the novel 7-membered lactams that successively fused with cyclopropane and cyclopentane rings was established to be trans-5,8,9,10,10a,10b-hexahydro-5-methylcyclopenta[3,4]cyclopropa[1,2-d]benzazepine-6,7-dione by X-ray crystallographic analysis. The pathways leading to the formation of all of these products arising from beta-scissions are discussed.

  DOI：

  10.1021/jo00028a037
• 作为产物：
  描述：

  2-氯喹啉 在 吡啶 、 盐酸 、 正丁基锂 、 水 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 56.0h， 生成 (2-氧代-1H-喹啉-3-基)乙酸酯
  参考文献：
  名称：

  3-乙酰氧基喹诺酮的对映选择性分子间[2 + 2]光环加成反应：（-）-吡啶啉酮的全合成。

  摘要：

  通过对映选择性分子间[2 + 2]光环加成反应为关键步骤，通过简明的路线（六个步骤，总收率17％）从3-乙酰氧基喹诺酮合成了天然产物（-）-pinolinone。

  DOI：

  10.1039/c3cc49469a

文献信息

• 2,2′-Biindolyl revisited. Synthesis and reactions
  作者：Jan Bergman、Eva Koch、Benjamin Pelcman

  DOI：10.1016/0040-4020(95)00223-u

  日期：1995.5

  An improved synthesis of 2,2′-biindolyl (1) is described. Derivatives of 1 with a variety of substituents in the 3,3′-positions, such as the 3,3′-diformyl derivative 19 have been synthesized. Potential syntheses of indolocarbazole alkaloids from such derivatives are outlined.

  描述了2,2'-联吲哚基（1）的改进的合成。已经合成了在3，3'-位置具有多个取代基的1的衍生物，例如3，3'-二甲酰基衍生物19。概述了由此类衍生物潜在合成吲哚并咔唑生物碱的方法。
• Madelung, Chemische Berichte, 1912, vol. 45, p. 3524
  作者：Madelung

  DOI：——

  日期：——
• Price; Smith, Australian Journal of Chemistry, 1956, vol. 9, p. 139
  作者：Price、Smith

  DOI：——

  日期：——
• Heller, Chemische Berichte, 1919, vol. 52, p. 743
  作者：Heller

  DOI：——

  日期：——
• Enantioselective, intermolecular [2+2] photocycloaddition reactions of 3-acetoxyquinolone: total synthesis of (−)-pinolinone
  作者：Florian Mayr、Christian Wiegand、Thorsten Bach

  DOI：10.1039/c3cc49469a

  日期：——

  The natural product (-)-pinolinone was synthesised via a concise route (six steps, 17% overall yield) from 3-acetoxyquinolone, employing an enantioselective intermolecular [2+2] photocycloaddition as the key step.

  通过对映选择性分子间[2 + 2]光环加成反应为关键步骤，通过简明的路线（六个步骤，总收率17％）从3-乙酰氧基喹诺酮合成了天然产物（-）-pinolinone。