ethyl 3-N-anthranylaminopropanoate | 6580-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-N-anthranylaminopropanoate
• 英文别名: ethyl 3-(naphthalen-1-ylamino)propanoate；N-Naphthyl-3-amino-propionsaeure-aethylester
• CAS: 6580-21-8
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: HQKMMNFHMNVRHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-N-anthranylaminopropanoate 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以25%的产率得到2-Azetidinone, 1-(1-naphthalenyl)-
  参考文献：
  名称：

  通过Fries型酸催化的1-芳基氮杂环丁烷-2-酮重排形成2,3-二氢-4（1 H）-喹诺酮及相关化合物

  摘要：

  各种1-芳基氮杂环丁烷-2-酮在回流下用三氟乙酸，100°C或浓的甲磺酸处理。通过酰基迁移和N–CO裂变生成硫酸，得到相应的2,3-二氢-4（1 H）-喹诺酮。在1-（3-取代的苯基）氮杂环丁烷-2-酮的情况下，获得两个位置异构产物，即5-和7-取代的2，3-二氢-4（1H）-喹诺酮。在酸性条件下，还将4-甲基-，4-乙氧基羰基-和4-哌啶-2-基-1-芳基氮杂环丁烷-2-酮及其类似物转化为相应的2-取代的2,3-二氢-4（1 H）-喹诺酮。 。3-取代的1-苯基氮杂环丁烷-2-酮（36）和（37）被转化为呋喃[3,2- c通过应用该方法分别制得]喹啉系统（38）和（40）。

  DOI：

  10.1039/p19800002105
• 作为产物：
  描述：

  3-溴丙酸乙酯 、 1-萘胺 以 乙醇 为溶剂， 反应 11.0h， 以45%的产率得到ethyl 3-N-anthranylaminopropanoate
  参考文献：
  名称：

  Synthesis and fluorescence properties of side-chain carboxylated 5,9-diaminobenzo[a]phenoxazinium salts

  摘要：

  The efficient synthesis of a series of novel side-chain carboxylated 5,9-diaminobenzo[a]phenoxazinium salts is described. The ring system was prepared by the reaction of 5-alkylamino-2-nitrosophenol hydrochlorides with the appropriate N-alkylated-naphthylamine. Evaluation of the visible and fluorescence properties of the cationic dyes was carried out in ethanol and water at physiological pH. In both solvents they showed intense visible absorption maxima in the range 500-638 nm (ethanol) and 625-650 (water), and fluoresced strongly, with fluorescence maxima from 612 to 669 nm (ethanol) and from 654 to 685 nm (water). A wide variation in fluorescence quantum yields is observed, ranging from 0.051 to 0.50 and 0.065 to 0.32 in ethanol and water, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.105

文献信息

• Rh ^III ‐Catalyzed Double Dehydrogenative Coupling of Free 1‐Naphthylamines with α,β‐Unsaturated Esters
  作者：Supriya Rej、Naoto Chatani

  DOI：10.1002/chem.202000706

  日期：2020.9

  of free 1‐naphthylamine and α,β‐unsaturated esters through C−H/C−H and C−H/N−H bonds is reported. The one step reaction leads to the formation of biologically important alkylidene‐1,2‐dihydrobenzo[cd]indoles scaffolds. This efficient process is much more synthetically convenient and useful than others because the starting materials, such as 1‐naphthylamine derivatives are readily available and the free

  据报道，Rh III催化游离的1-萘胺与α，β-不饱和酯通过CH / CH / CH和CH / NH键进行连续的CH-CH双氧化反应。一步反应导致形成生物学上重要的亚烷基-1，2-二氢苯并[ cd ]吲哚骨架。这种高效的方法在合成上比其他方法更加方便和有用，因为起始材料（例如1-萘胺衍生物）很容易获得，而游离胺充当引导基团。
• KANO SHINZO; EBATA TSUTOMU; SHIBUYA SHIROSHI, J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 10, 2105-2111
  作者：KANO SHINZO、 EBATA TSUTOMU、 SHIBUYA SHIROSHI

  DOI：——

  日期：——
• MYLARI, BANAVARA L.;BEYER, THOMAS A.;SIEGEL, TODD W., J. MED. CHEM., 34,(1991) N, C. 1011-1018
  作者：MYLARI, BANAVARA L.、BEYER, THOMAS A.、SIEGEL, TODD W.

  DOI：——

  日期：——
• Formation of 2,3-dihydro-4(1H)-quinolones and related compounds via Fries-type acid-catalysed rearrangement of 1-arylazetidin-2-ones
  作者：Shinto Kano、Tsutomu Ebata、Shiroshi Shibuya

  DOI：10.1039/p19800002105

  日期：——

  corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N–CO fission. In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl-, 4-ethoxycarbonyl-, and 4-piperidin-2yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3dihydro-4(1H)-quinolones

  各种1-芳基氮杂环丁烷-2-酮在回流下用三氟乙酸，100°C或浓的甲磺酸处理。通过酰基迁移和N–CO裂变生成硫酸，得到相应的2,3-二氢-4（1 H）-喹诺酮。在1-（3-取代的苯基）氮杂环丁烷-2-酮的情况下，获得两个位置异构产物，即5-和7-取代的2，3-二氢-4（1H）-喹诺酮。在酸性条件下，还将4-甲基-，4-乙氧基羰基-和4-哌啶-2-基-1-芳基氮杂环丁烷-2-酮及其类似物转化为相应的2-取代的2,3-二氢-4（1 H）-喹诺酮。 。3-取代的1-苯基氮杂环丁烷-2-酮（36）和（37）被转化为呋喃[3,2- c通过应用该方法分别制得]喹啉系统（38）和（40）。
• Synthesis and fluorescence properties of side-chain carboxylated 5,9-diaminobenzo[a]phenoxazinium salts
  作者：Vânia H.J. Frade、M. Sameiro T. Gonçalves、João C.V.P. Moura

  DOI：10.1016/j.tetlet.2005.05.105

  日期：2005.7

  The efficient synthesis of a series of novel side-chain carboxylated 5,9-diaminobenzo[a]phenoxazinium salts is described. The ring system was prepared by the reaction of 5-alkylamino-2-nitrosophenol hydrochlorides with the appropriate N-alkylated-naphthylamine. Evaluation of the visible and fluorescence properties of the cationic dyes was carried out in ethanol and water at physiological pH. In both solvents they showed intense visible absorption maxima in the range 500-638 nm (ethanol) and 625-650 (water), and fluoresced strongly, with fluorescence maxima from 612 to 669 nm (ethanol) and from 654 to 685 nm (water). A wide variation in fluorescence quantum yields is observed, ranging from 0.051 to 0.50 and 0.065 to 0.32 in ethanol and water, respectively. (c) 2005 Elsevier Ltd. All rights reserved.