3-(N-乙基-N-苯基氨基)-3-氧代丙酸甲酯 | 142613-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(N-乙基-N-苯基氨基)-3-氧代丙酸甲酯
• 英文名称: methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate
• 英文别名: methyl 3-(ethyl(phenyl)amino)-3-oxopropanoate；Methyl 3-(ethyl(phenyl)amino)-3-oxo-propanoate；methyl 3-(N-ethylanilino)-3-oxopropanoate
• CAS: 142613-14-7
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: GVBMXLRNNXXMRY-UHFFFAOYSA-N

物化性质

• 沸点：
  323.0±25.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(N-乙基-N-苯基氨基)-3-氧代丙酸甲酯 在 吡啶 、 水 、 sodium methylate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 拉喹莫德
  参考文献：
  名称：

  [EN] INTERMEDIATE COMPOUNDS AND PROCESSES FOR THE PREPARATION OF QUINOLINE DERIVATIVES SUCH AS LAQUINIMOD SODIUM
  [FR] COMPOSÉS INTERMÉDIAIRES ET PROCÉDÉS DE PRÉPARATION DE DÉRIVÉS DE QUINOLÉINE TELS QUE LAQUINIMOD SODIUM

  摘要：

  本发明涉及制备喹啉-3-羧酰胺衍生物的工艺，例如5-氯-3-(乙基苯基氨基甲酰)-1-甲基-2-氧代-1,2-二氢喹啉-4-酸钠盐（拉奎尼莫钠）。本发明还涉及在这些过程中形成的中间体。

  公开号：

  WO2012070051A1
• 作为产物：
  描述：

  N-苯基香豆甲酯 在 吡啶 、 氢氧化钾 、 四丁基碘化铵 、 sodium hydride 、 肼 作用下， 反应 2.0h， 生成 3-(N-乙基-N-苯基氨基)-3-氧代丙酸甲酯
  参考文献：
  名称：

  Dirhodium tetraacetate catalyzed carbon-hydrogen insertion reaction in N-substituted .alpha.-carbomethoxy-.alpha.-diazoacetanilides and structural analogs. Substituent and conformational effects

  摘要：

  A series of acyclic alpha-carbomethoxy-alpha-diazoacetanilides with different N-substituents, 5a-k, was prepared and the rhodium(II) acetate catalyzed reactions studied. It was found that the rhodium carbenoid reaction with these compounds occurred only at the N-substituent; when the N-substituent is a propargyl group, rhodium carbenoid addition to the triple bond is favored, resulting, ultimately, in the formation of a bicyclic furan derivative 8. With an N-(tert-butyloxycarbonyl)methyl substituent, interception of the rhodium carbenoid by the ester carbonyl oxygen occurred preferentially to give, eventually, 1,4-oxazine derivatives 9 and 9'. For N-alkyl substituents, rhodium carbenoid carbon-hydrogen (C-H) insertion into the alkyl group to give 2-azetidinone and/or 2-pyrrolidinone derivatives was observed. The chemoselectivity of the rhodium carbenoid C-H insertion can be altered by the use of the alpha-acetyl and alpha-phenylsulfonyl substituents. In these cases, exclusive C-H insertion at the N-aryl moiety resulted to give 2(3H)-indolinone products. However, the alpha-substituent effect on the chemoselectivity of the insertion reaction is easily overridden by conformational effects about the amide N-C(O) bond as revealed by the insertion reactions of the conformationally rigid compounds 20a-c. The alpha-substituent effects are reestablished when conformational rigidity is removed, as exemplified by the rhodium carbenoid insertion reactions of compounds 29a,b.

  DOI：

  10.1021/jo00042a018

文献信息

• Development of a Practical and Reliable Synthesis of Laquinimod
  作者：Johan Wennerberg、Anders Björk、Tomas Fristedt、Bo Granquist、Karl Jansson、Ingela Τhuvesson

  DOI：10.1021/op700001c

  日期：2007.7.1

  Laquinimod (5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinoline carboxamide) is a drug candidate for treatment of Multiple Sclerosis. A short and industrially feasible process for the preparation of laquinimod starting from 2-amino-6-chlorobenzoic acid, in essentially four steps, is dis-cussed. The key step is a novel reaction in which a methyl ester is converted to an amide

  拉喹莫德（5-氯-1,2-二氢-N-乙基-4-羟基-1-甲基-2-氧代-N-苯基-3-喹啉羧酰胺）是治疗多发性硬化症的候选药物。讨论了从2-氨基-6-氯苯甲酸开始制备拉喹莫德的短的且工业上可行的方法，该方法基本上以四个步骤进行。关键步骤是一个新颖的反应，其中甲酯以非常高的收率和极好的纯度转化为酰胺。本文阐明了放大过程以及安全性方面以及中间体和产品的杂质分布。描述了初始实验室条件，以及转移到中试规模后所做的更改。
• Inhibitors of VEGF receptor and HGF receptor signaling
  申请人：Saavedra Mario Oscar

  公开号：US20070004675A1

  公开（公告）日：2007-01-04

  The invention relates to the inhibition of VEGF receptor signaling and HGF receptor signaling. The invention provides compounds and methods for inhibiting VEGF receptor signaling and HGF receptor signaling. The invention also provides compositions and methods for treating cell proliferative diseases and conditions

  该发明涉及抑制VEGF受体信号和HGF受体信号。该发明提供了抑制VEGF受体信号和HGF受体信号的化合物和方法。该发明还提供了治疗细胞增殖性疾病和病况的组合物和方法。
• Palladium-catalysed intramolecular carbenoid insertion of α-diazo-α-(methoxycarbonyl)acetanilides for oxindole synthesis
  作者：Daniel Solé、Ferran Pérez-Janer、Israel Fernández

  DOI：10.1039/c7cc00718c

  日期：——

  A novel, selective palladium-catalysed carbenoid C(aryl)-H insertion of [small alpha]-diazo-[small alpha]-(methoxycarbonyl)acetanilides leading to oxindoles is described.

  描述了新颖的，选择性的钯催化的生成的小α-重氮-[小α]-（甲氧羰基）乙酰胺的钯催化类胡萝卜素C（芳基）-H插入。
• INHIBITORS OF VEGF RECEPTOR AND HGF RECEPTOR SIGNALING
  申请人：Saavedra Oscar Mario

  公开号：US20120083482A1

  公开（公告）日：2012-04-05

  The invention relates to the inhibition of VEGF receptor signaling and HGF receptor signaling. The invention provides compounds of general formula (A) wherein A 1 is sulfur, A 3 is CH, A 2 is CH, D is heterocycle, Z is oxygen, SO 0-2 or NR, Ar is phenyl and G is not a ring, and methods for inhibiting VEGF receptor signaling and HGF receptor signaling. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制VEGF受体信号和HGF受体信号的技术。本发明提供了通式（A）的化合物，其中A1为硫，A3为CH，A2为CH，D为杂环，Z为氧，SO0-2或NR，Ar为苯基，G不是环，并提供了抑制VEGF受体信号和HGF受体信号的方法。本发明还提供了治疗细胞增殖性疾病和病情的组合物和方法。
• Intermediate compounds and processes for the preparation of quinoline derivatives such as Laquinimod sodium
  申请人：Marom Ehud

  公开号：US08865742B2

  公开（公告）日：2014-10-21

  The present invention relates to processes for the preparation of quinoline-3-carboxamide derivatives, such as sodium 5-chloro-3-(ethylphenylcarbamoyl)-1-methyl-2-oxo-1,2-dihydroquinolin-4-olate (Laquinimod sodium). The present invention further relates to intermediates formed in such processes.

  本发明涉及制备喹啉-3-羧酰胺衍生物的过程，例如5-氯-3-(乙基苯基氨甲酰)-1-甲基-2-氧代-1,2-二氢喹啉-4-酸钠盐（拉奎尼莫钠）。本发明还涉及在这些过程中形成的中间体。