dimethyl acetamidomalonate sodium salt | 72071-39-7

• 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: dimethyl acetamidomalonate sodium salt
• CAS: 72071-39-7
• 化学式: C₇H₁₀NNaO₅
• 分子量: 211.15
• InChiKey: CFGPOVHURZTMBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.84
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  65.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl acetamidomalonate sodium salt 、 4-(Bromomethyl)-2-(methoxymethyl)-5-propan-2-yl-1,2-oxazol-3-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以73%的产率得到Dimethyl 2-acetamido-2-[[2-(methoxymethyl)-3-oxo-5-propan-2-yl-1,2-oxazol-4-yl]methyl]propanedioate
  参考文献：
  名称：

  Excitatory amino-acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid

  摘要：

  We have previously proposed the existence of a lipophilic cavity of the 2-amino-3-(3-hydroxy-5-methylisoxazol4-yl)propionic acid (AMPA) receptor recognition site capable of accommodating alkyl substituents of limited size in the 5-position of the isoxazole ring. In order to indirectly elucidate the approximate extent of this proposed cavity we have synthesized and pharmacologically characterized a number of AMPA analogues. For most of these AMPA analogues, a positive correlation between AMPA receptor affinity and agonist effect was observed. The only exception was demethyl-AMPA (8a), which showed relatively high AMPA receptor affinity (IC50 = 0.27 mu M) but remarkably weak agonist potency (EC50 = 900 mu M). Whereas the ethyl analogue of AMPA (Et-AMPA) (IC50 = 0.030 mu M; EC50 = 2.3 mu M) has previously been shown to be slightly more potent than AMPA (IC50 = 0.040 mu M; EC50 = 3.5 mu M), substitutions of a propyl or a butyl group for the methyl group of AMPA to give 8b (IC50 = 0.090 mu M; EC50 = 5.0 mu M) or 8f (IC50 = 1.0 mu M; EC50 = 32 mu M), respectively, result in progressive loss of the AMPA agonist effect. Analogues containing larger groups, such as isopentyl (8e), 1-propylbutyl (8g), 2,2-dimethylpropyl (8h), or benzyl (14) groups, were very weak or totally inactive as AMPA receptor ligands.

  DOI：

  10.1016/s0223-5234(97)89085-x

文献信息

• Palladium-catalyzed asymmetric alkylation via π-allyl intermediate: Acetamidomalonate ester as a nucleophile.
  作者：Motowo Yamaguchi、Toshihide Shima、Takamichi Yamagishi、Mitsuhiko Hida

  DOI：10.1016/s0040-4039(00)97803-1

  日期：1990.1

  Asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with sodium salt of acetamidomalonate ester has been carried out in the presence of a palladium catalyst containing (S)-BINAP to give a chiral α-allyl-αacetamidomalonate ester derivative of high optical purity (94±1% ee).

  在含有（S）-BINAP的钯催化剂的存在下，已将1,3-二苯基-2-丙烯基乙酸乙酸酯与乙酰氨基丙酸酯的钠盐进行不对称烯丙基烷基化反应，得到高光学纯度（94±1％ee）。
• Construction of P-stereogenic center by selective ligation of NPN type ligands and application to asymmetric allylic substitution reactions
  作者：Takamichi Yamagishi、Masatoshi Ohnuki、Takahiro Kiyooka、Dai Masui、Kiyoshi Sato、Motowo Yamaguchi

  DOI：10.1016/j.tetasy.2003.09.004

  日期：2003.10

  Chiral bisoxazolylphosphine ligands 1 [(S,S)-PhP(Ox-R)(2): R = Me, Pr-i, Bu-t] with an N-P-N backbone were prepared from chiral 4-alkyl-2-phenyl-4,5-dihydrooxazole compounds. These ligands coordinated to Pd(II) ion as bidentate ligands selectively to give a stereogenic phosphorus atom. The Pd-(S,S)-PhP(Ox-Bu-t)(2) 1c catalyst evoked high enantioselectivity in asymmetric allylic substitutions of acyclic substrates using dimethyl sodiomalonate as nucleophile. In the reaction of 3-penten-2-yl acetate, which affords a pi-allyl intermediate with a small steric factor, the Pd-1c catalyst successfully induced very high enantioselectivity (94% ee) indicating the effectiveness of the P-stereogenic center formed by selective ligation of ligand 1. In the reaction of cyclic substrates, moderate to high enantioselectivity was obtained by Pd-1 catalyst using the sodium salt of dimethyl methylmalonate. (C) 2003 Elsevier Ltd. All rights reserved.
• Palladium-assisted C-glycosylation. Addition of carbanions to cyclic enol ethers
  作者：Lois V. Dunkerton、Anthony J. Serino

  DOI：10.1021/jo00135a035

  日期：1982.7
• Excitatory amino-acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid
  作者：F.A. Sløk、B Ebert、Y Lang、P Krogsgaard-Larsen、S.M. Lenz、U Madsen

  DOI：10.1016/s0223-5234(97)89085-x

  日期：1997.1

  We have previously proposed the existence of a lipophilic cavity of the 2-amino-3-(3-hydroxy-5-methylisoxazol4-yl)propionic acid (AMPA) receptor recognition site capable of accommodating alkyl substituents of limited size in the 5-position of the isoxazole ring. In order to indirectly elucidate the approximate extent of this proposed cavity we have synthesized and pharmacologically characterized a number of AMPA analogues. For most of these AMPA analogues, a positive correlation between AMPA receptor affinity and agonist effect was observed. The only exception was demethyl-AMPA (8a), which showed relatively high AMPA receptor affinity (IC50 = 0.27 mu M) but remarkably weak agonist potency (EC50 = 900 mu M). Whereas the ethyl analogue of AMPA (Et-AMPA) (IC50 = 0.030 mu M; EC50 = 2.3 mu M) has previously been shown to be slightly more potent than AMPA (IC50 = 0.040 mu M; EC50 = 3.5 mu M), substitutions of a propyl or a butyl group for the methyl group of AMPA to give 8b (IC50 = 0.090 mu M; EC50 = 5.0 mu M) or 8f (IC50 = 1.0 mu M; EC50 = 32 mu M), respectively, result in progressive loss of the AMPA agonist effect. Analogues containing larger groups, such as isopentyl (8e), 1-propylbutyl (8g), 2,2-dimethylpropyl (8h), or benzyl (14) groups, were very weak or totally inactive as AMPA receptor ligands.