2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid methyl ester | 78941-89-6

• 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: 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid methyl ester
• 英文别名: methyl 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylate；3,4-dihydro-4-methoxycarbonyl-2-quinolinone；methyl 1-(2-oxo-4-quinolyl)formate；2-oxo-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester；2-Oxo-1,2,3,4-tetrahydro-chinolin-4-carbonsaeure-methylester；methyl 2-oxo-3,4-dihydro-1H-quinoline-4-carboxylate
• CAS: 78941-89-6
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD11935978
• 分子量: 205.213
• InChiKey: XSQXXTZNJGFELQ-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  355.8±42.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为产物：
  描述：

  吲哚-3-乙腈 在 盐酸 、 2,2'-联吡啶 、 palladium(II) trifluoroacetate 、 二甲基亚砜 、 苯磺酸 作用下， 以 水 为溶剂， 反应 36.0h， 生成 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid methyl ester
  参考文献：
  名称：

  钯催化腈的三组分级联反应：合成 2-Arylquinoline-4-carboxylates

  摘要：

  报道了一种将易于获得的起始材料 2-(2-oxoindolin-3-yl) 乙腈、芳基硼酸和醇类转化为 2-芳基喹啉-4-羧酸酯的新方法。该过程涉及在温和条件下在具有高官能团耐受性的 Pd(II) 催化剂存在下的三组分加成/扩环/酯化反应。此外，研究了所得产物的光物理性质，并表现出优异的极性敏感荧光性质和 AIE 性质。

  DOI：

  10.1021/acs.orglett.1c02962

文献信息

• Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles
  作者：Oscar R. Suárez-Castillo、Claudia I. Bautista-Hernández、Maricruz Sánchez-Zavala、Myriam Meléndez-Rodríguez、Araceli Sierra-Zenteno、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.3987/com-12-12472

  日期：——

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.
• Fuchs, Peter; Hess, Ulrich; Holst, Hans Henrik, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 185 - 192
  作者：Fuchs, Peter、Hess, Ulrich、Holst, Hans Henrik、Lund, Henning

  DOI：——

  日期：——
• Convergent synthesis of dihydroquinolones from o-aminoarylboronates
  作者：Joachim Horn、Ho Yin Li、Stephen P. Marsden、Adam Nelson、Rachel J. Shearer、Amanda J. Campbell、David House、Gordon G. Weingarten

  DOI：10.1016/j.tet.2009.06.103

  日期：2009.10

  An efficient and convergent one-step synthesis of substituted dihydroquinolin-2-ones from alpha,beta-unsaturated esters and aminoaryl pinacolboronates under rhodium catalysis is reported. The reaction is easily applicable in parallel synthesis format and provides convenient access to this pharmaceutically-relevant motif. (C) 2009 Elsevier Ltd. All rights reserved.
• Dimethyl malonate as a one-carbon source: a novel method of introducing carbon substituents onto aromatic nitro compounds
  作者：N Selvakumar、B Yadi Reddy、G Sunil Kumar、Javed Iqbal

  DOI：10.1016/s0040-4039(01)01809-3

  日期：2001.11

  A number of carbon substituents possessing various functional groups could be introduced onto aromatic nitro compounds using dimethyl malonate as a one-carbon source and linker. Decarboxylation of both the ester groups originating from dimethyl malonate in this methodology is particularly significant. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Aeschlimann, Journal of the Chemical Society, 1926, p. 2908
  作者：Aeschlimann

  DOI：——

  日期：——