ethyl 2-(2-furoyl)-N,N-dimethylglycinate | 120133-85-9

• 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 2-(2-furoyl)-N,N-dimethylglycinate
• 英文别名: ethyl N,N-dimethylfuranylglycianate
• CAS: 120133-85-9
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: QDSMBCQBCSULOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (1'R*,5S*)-5-<1'-amino-1'-methyl>ethoxycarbonylmethyl-4-ethoxycarbonyl-5-(2'-furyl)-4,5-dihydrooxazole 在 sodium tetrahydroborate 、 草酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 53.0h， 生成 ethyl 2-(2-furoyl)-N,N-dimethylglycinate
  参考文献：
  名称：

  Diastereoselective synthesis of syn,syn- and syn,anti-2,4-diamino-3-hydroxyglutaric acid derivatives from ethyl α-acyl alaninates

  摘要：

  Syn,syn- and syn,anti-isomers of the four possible diastereomers of O,N,N'-protected 2,4-diamino-3-hydroxyglutaric acid derivatives 3-7 were diastereoselectively obtained. Syn,syn isomers of oxazolines 3 were selectively achieved by an aldol-like reaction in protic conditions between a-metallated ethyl isocyanoacetate 1 and alpha-acyl alaninates 2. Derivatives 4 with a syn,anti-configuration were obtained under epimerization reaction conditions, whereas derivatives 5-7 with syn,syn-configuration were selectively obtained under kinetic reaction conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00065-4

文献信息

• The synthesis of amino acids by reaction of an electrophilic glycine cation equivalent with neutral carbon nucleophiles
  作者：Martin J. O'Donnell、William D. Bennett

  DOI：10.1016/s0040-4020(01)86045-2

  日期：1988.1

  Seven neutral carbon nucleophiles (active aromatics, allylsilanes, and a silyl enol ether) were reacted with the glycine cation equivalent 12 in the presence of TiCl4to yield α-substituted amino acid derivatives in moderate yield (1 - 61.5 mmolar scale). Deprotection of the Schiff base ester products led to the corresponding amino acids.

  在TiCl 4的存在下，使七个中性碳亲核试剂（活性芳族化合物，烯丙基硅烷和甲硅烷基烯醇醚）与甘氨酸阳离子当量12反应，以中等收率（1-61.5 mmolar规模）产生α-取代的氨基酸衍生物。Schiff碱酯产物的脱保护得到相应的氨基酸。