ethyl 1-amino-3-phenyl-2-naphthoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-amino-3-phenyl-2-naphthoate
• 英文别名: Ethyl 1-amino-3-phenylnaphthalene-2-carboxylate
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: NJPKCHLUTJYKRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲基苯腈 在 palladium on activated charcoal lithium diisopropyl amide 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 生成 ethyl 1-amino-3-phenyl-2-naphthoate
  参考文献：
  名称：

  通过连续的迈克尔加成/乙醇酸酯-腈偶联途径高效合成1-氨基-2-萘甲酸衍生物，并将其用于方便地制备芳基萘并呋喃酮木质素的9-氨基类似物。

  摘要：

  通过在二甘醇二甲醚中用LDA处理2-烷基苄腈与α，β-不饱和羧酸酯和腈反应原位生成的2-（α-硫代烷基）苄腈与1-氨基-3,4-二氢-2-萘甲酸乙酯和通过将硫代腈迈克尔加成到α，β-不饱和羧酸衍生物上，然后碘化锌促进分子内烯醇盐-腈偶联，生成的烯醇盐中间体以54-98％的产率形成腈。在回流的对甲基苯甲基中用活性炭上的钯脱氢，将二氢萘羧酸衍生物以43-99％的产率转化为相应的1-氨基-2-萘甲酸衍生物。随后，我们表明，通过使用类似的反应顺序，

  DOI：

  10.1021/jo961744r

文献信息

• An Efficient General Synthesis of 1-Amino-2-naphthalenecarboxylic Acid Derivatives Based on a Tandem Conjugate Addtion-Enolate Nitrile Coupling Sequence
  作者：Kazuhiro Kobayashi、Keiichiro Takada、Hiroto Tanaka、Tomokazu Uneda、Tomohide Kitamura、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/cl.1996.25

  日期：1996.1

  Reaction of o-(α-lithioalkyl)benzonitriles with α,β-unsaturated carboxylic acid derivatives produced 1-amino-3,4-dihydro-2-naphthalenecarboxylic acid derivatives through the tandem conjugate addition-enolate nitrile coupling sequence, which in turn were converted into 1-amino-2-naphthalenecarboxylic acid derivatives on dehydrogenation with palladium on activated carbon.

  o-(α-锂烷基)苯腈与α,β-不饱和羧酸衍生物的反应通过串联的共轭加成-烯醇腈偶联序列生成1-氨基-3,4-二氢-2-萘甲酸衍生物，而这些衍生物在与活性炭铂的脱氢反应中进一步转化为1-氨基-2-萘甲酸衍生物。
• Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles
  作者：Yan He、Xinying Zhang、Xuesen Fan

  DOI：10.1039/c4cc01738b

  日期：——

  cascade process occurred to give 9-aminonaphtho[2,3-c]furan-1(3H)-ones in good yields. By using this tandem reaction as a key step, a concise and versatile synthetic strategy for the total synthesis of arylnaphthalene lactone lignans has been developed.

  2-炔基苄腈与Reformatsky试剂的串联反应被证明是一种针对1-氨基萘-2-羧酸酯的新颖而有效的方法。有趣的是，以2-（3-羟基丙-1-炔基）苄腈为底物，发生了更复杂的级联过程，以高收率得到了9-氨基萘[2,3-c]呋喃-1（3H）-。通过将该串联反应用作关键步骤，已开发出用于全合成芳基萘内酯木脂素的简洁而通用的合成策略。
• Synthesis of 1-Amino-2-naphthalenecarboxylic Acid Derivatives via the Intramolecular Cyclization of 4-(2-Cyanophenyl)-2-butenoic Acid Derivatives and Its Application to the One-Pot Preparation of Benzo[<i>h</i>]quinazoline-2,4(1<i>H</i>,3<i>H</i>)-diones
  作者：Kazuhiro Kobayashi、Hiroto Tanaka、Harumi Takabatake、Tomohide Kitamura、Ryoji Nakahashi、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.72.1071

  日期：1999.5

  The reaction of 2-(lithiomethyl)benzonitrile with 2-phenylthio-2-alkenoic acid derivatives in diglyme at −78 °C, followed by oxidation with sodium metaperiodate in aqueous MeOH at room temperature and the subsequent elimination reaction in refluxing toluene, gave 4-(2-cyanophenyl)-2-butenoic acid derivatives in moderate-to-fair overall yields. Intramolecular cyclization of these products using NaH in DMF at 0 °C gave 1-amino-2-naphthalenecarboxylic acid derivatives almost quantitatively. Successive treatments with an isocyanate without isolation of the aminonaphthalenecarboxylates under reflux afforded benzo[h]quinazoline-2,4(1H,3H)-diones in moderate-to-good yields.

  2- (lithiomethyl)苯甲腈与 2-苯硫基-2-烯酸衍生物在-78 °C的二甘醇中反应，然后在室温下用偏碘酸钠在水性 MeOH 中氧化，随后在回流甲苯中进行消去反应，得到 4-(2-氰基苯基)-2-丁烯酸衍生物，总产率中等至一般。在 0 °C 的 DMF 中使用 NaH 对这些产物进行分子内环化，几乎定量地得到了 1-氨基-2-萘甲酸衍生物。在不分离氨基萘甲酸酯的情况下，用异氰酸酯在回流条件下连续处理，可得到苯并[h]喹唑啉-2,4(1H,3H)-二酮，收率为中等至良好。
• Synthesis of Naphthalene Amino Esters by the Blaise Reaction of <i>o</i>-Alkynylarenenitriles
  作者：Karuppusamy Sakthivel、Kannupal Srinivasan

  DOI：10.1021/jo500137m

  日期：2014.4.4

  The action of a Reformatsky reagent on o-alkynylarenenitriles provides a convenient access to naphthalene amino esters via tandem 6-endo-dig carbannulation of in situ generated Blaise reaction intermediates. The products are formed in moderate to good yields with high chemo- and regioselectivity.
• Efficient Synthesis of 1-Amino-2-naphthalenecarboxylic Acid Derivatives via a Sequential Michael Addition/Enolate−Nitrile Coupling Route and Its Application to Facile Preparation of 9-Amino Analogues of Arylnaphthofuranone Lignans
  作者：Kazuhiro Kobayashi、Tomokazu Uneda、Keiichiro Takada、Hiroto Tanaka、Tomohide Kitamura、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1021/jo961744r

  日期：1997.2.1

  2-alkylbenzonitriles with LDA in diglyme, with alpha,beta-unsaturated carboxylates and nitriles produced 1-amino-3,4-dihydro-2-naphthalenecarboxylates and carbonitriles in 54-98% yields through Michael addition of the lithio nitriles to alpha,beta-unsaturated carboxylic acid derivatives, followed by zinc iodide-promoted intramolecular enolate-nitrile coupling of the resulting enolate intermediates. The

  通过在二甘醇二甲醚中用LDA处理2-烷基苄腈与α，β-不饱和羧酸酯和腈反应原位生成的2-（α-硫代烷基）苄腈与1-氨基-3,4-二氢-2-萘甲酸乙酯和通过将硫代腈迈克尔加成到α，β-不饱和羧酸衍生物上，然后碘化锌促进分子内烯醇盐-腈偶联，生成的烯醇盐中间体以54-98％的产率形成腈。在回流的对甲基苯甲基中用活性炭上的钯脱氢，将二氢萘羧酸衍生物以43-99％的产率转化为相应的1-氨基-2-萘甲酸衍生物。随后，我们表明，通过使用类似的反应顺序，