2-phenylmalonamic acid ethyl ester | 1190830-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenylmalonamic acid ethyl ester
• 英文别名: methyl 3-amino-3-oxo-2-phenylpropanoate
• CAS: 1190830-34-2
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: JCKUPQHTQFBNPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  偶氮二甲酸二叔丁酯 、 2-phenylmalonamic acid ethyl ester 在 (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide 、 lanthanum(III) nitrate hexahydrate 、 D-valine t-butyl ester 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以92%的产率得到(R)-di-tert-butyl 1-(1-amino-3-methoxy-1,3-dioxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Managing Highly Coordinative Substrates in Asymmetric Catalysis: A Catalytic Asymmetric Amination with a Lanthanum-Based Ternary Catalyst

  摘要：

  Full details of a catalytic asymmetric amination with a lanthanum/amide-based ligand catalyst system are described. A catalyst comprising La(NO3)(3)center dot 6H(2)O, (R)-3a and H-D-Val-V'Bu was identified to promote the catalytic asymmetric amination of nonprotected succinimide derivative 1 with as little as 1 mol % catalyst loading Mechanistic studies by various spectroscopic analyses and several control and kinetic experiments suggested that the catalyst components were in equilibrium between the associated and dissociated forms, and that the reaction likely proceeded through a La(NO3)(3)center dot 6H(2)O/(R)-3a/H-D-Val-O'Bu ternary complex. This catalyst system was also effective for asymmetric amination of N-nonsubstituted alpha-alkoxycarbonyl amides 7, hitherto unprecedented substrates in asymmetric catalysis, probably due to their attenuated reactivity and difficult stereocontrol, affording the amination products in up to > 99% yield and > 99% ee. The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.

  DOI：

  10.1021/ja9052653
• 作为产物：
  描述：

  methyl 2-cyano-2-phenylacetate 在 二乙基羟胺 、 水 、 copper diacetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到2-phenylmalonamic acid ethyl ester
  参考文献：
  名称：

  乙酸铜（II）催化腈的温和水合

  摘要：

  描述了一种简单，温和且通用的程序，该程序使用铜作为催化剂并由N，N-二乙基羟胺促进将腈水合为酰胺。该反应可以在水中进行。

  DOI：

  10.1039/c5cc08714g

文献信息

• [EN] ANTICOAGULANT ANTIDOTES<br/>[FR] ANTIDOTES D'ANTICOAGULANTS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011089183A2

  公开（公告）日：2011-07-28

  The present invention relates to antibody molecules against anticoagulants, in particular dabigatran, and their use as antidotes of such anticoagulants.
• A mild hydration of nitriles catalysed by copper(<scp>ii</scp>) acetate
  作者：Patricia Marcé、James Lynch、A. John Blacker、Jonathan M. J. Williams

  DOI：10.1039/c5cc08714g

  日期：——

  A simple, mild and general procedure for the hydration of nitriles to amides using copper as catalyst and promoted by N,N-diethylhydroxylamine is described. The reaction can be conducted in water...

  描述了一种简单，温和且通用的程序，该程序使用铜作为催化剂并由N，N-二乙基羟胺促进将腈水合为酰胺。该反应可以在水中进行。
• Managing Highly Coordinative Substrates in Asymmetric Catalysis: A Catalytic Asymmetric Amination with a Lanthanum-Based Ternary Catalyst
  作者：Tomoyuki Mashiko、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/ja9052653

  日期：2009.10.21

  Full details of a catalytic asymmetric amination with a lanthanum/amide-based ligand catalyst system are described. A catalyst comprising La(NO3)(3)center dot 6H(2)O, (R)-3a and H-D-Val-V'Bu was identified to promote the catalytic asymmetric amination of nonprotected succinimide derivative 1 with as little as 1 mol % catalyst loading Mechanistic studies by various spectroscopic analyses and several control and kinetic experiments suggested that the catalyst components were in equilibrium between the associated and dissociated forms, and that the reaction likely proceeded through a La(NO3)(3)center dot 6H(2)O/(R)-3a/H-D-Val-O'Bu ternary complex. This catalyst system was also effective for asymmetric amination of N-nonsubstituted alpha-alkoxycarbonyl amides 7, hitherto unprecedented substrates in asymmetric catalysis, probably due to their attenuated reactivity and difficult stereocontrol, affording the amination products in up to > 99% yield and > 99% ee. The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.