3-氰基-2-乙基-3-羟基丁酸乙酯 | 247098-17-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-氰基-2-乙基-3-羟基丁酸乙酯
• 中文别名: 格列美脲杂质6
• 英文名称: ethyl 2-ethyl-3-oxobutanoate cyanohydrin
• 英文别名: ethyl-α-ethylacetoacetate cyanohydrin；2-ethyl-3-cyano-3-hydroxy-butyric acid ethyl ester；2-Aethyl-3-cyan-3-hydroxy-buttersaeure-aethylester；α-Methyl-β-aethyl-aepfelsaeure-β-aethylester-α-nitril；α-Aethyl-acetessigsaeure-aethylester-cyanhydrin；Butanoic acid, 3-cyano-2-ethyl-3-hydroxy-, ethyl ester；ethyl 3-cyano-2-ethyl-3-hydroxybutanoate
• CAS: 247098-17-5
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: HTIIZCVGZUEJQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氰基-2-乙基-3-羟基丁酸乙酯 在 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 2-乙基乙酰乙酸乙酯
  参考文献：
  名称：

  Bhandari, Kalpana; Sharma, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 11, p. 2467 - 2470

  摘要：

  DOI：
• 作为产物：
  描述：

  氰化钠 、 2-乙基乙酰乙酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到3-氰基-2-乙基-3-羟基丁酸乙酯
  参考文献：
  名称：

  Total synthesis of cis and trans-hydroxyglimepiride: active metabolite of glimepiride

  摘要：

  Syntheses of trans-hydroxyglimepiride 2b, a human metabolite of the blood glucose lowering agent glimepiride I and its corresponding cis-stereoisomer 2a, are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01145-6

文献信息

• Relative stereochemistry of the A ring of plant bile pigments
  作者：Robert W. Schoenleber、Youseung Kim、Henry Rapoport

  DOI：10.1021/ja00321a026

  日期：1984.5

  synthesis and characterization, including the stereochemistry, of a series of 3,4-dihydropyrromethenones and 2,3-dihydrodioxobilins are described. High-resolution /sup 1/H NMR spectral analysis allows the determination of the A ring coupling constants for a series of cis and trans model compounds. From these data and correlations, the relative stereochemistry in the A ring of phycocyanin and similar bile

  描述了一系列 3,4-dihydropyrromethenones 和 2,3-dihydrodioxobilins 的合成和表征，包括立体化学。高分辨率 /sup 1/H NMR 光谱分析允许确定一系列顺式和反式模型化合物的 A 环耦合常数。根据这些数据和相关性，可以得出藻蓝蛋白 A 环中的相对立体化学和类似胆色素结构的结论。
• Kuester, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1927, vol. 172, p. 242
  作者：Kuester

  DOI：——

  日期：——
• Diastereoselective synthesis of phycocyanobilin-cysteine adducts
  作者：John E. Bishop、Jon O. Nagy、John F. O'Connell、Henry Rapoport

  DOI：10.1021/ja00021a032

  日期：1991.10

  Methodology is presented for the synthesis of two diastereomers of a cysteine-linked phycocyanobilin derivative. The crucial reaction is a diastereoselective 1,6-Michael addition of cysteine methyl ester to an appropriate dihydropyrromethenone educt. The diastereomers so generated were then elaborated to two phycocyanobilin trimethyl esters. Definitive assignments of relative stereochemistry, double bond geometry, and solution conformation are accomplished by application of ROESY NMR experiments, while absolute stereochemical assignments are based on degradation to compounds of known chirality.
• Plieninger; Decker, Justus Liebigs Annalen der Chemie, 1956, vol. 598, p. 198,205
  作者：Plieninger、Decker

  DOI：——

  日期：——
• Bhandari, Kalpana; Sharma, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 11, p. 2467 - 2470
  作者：Bhandari, Kalpana、Sharma

  DOI：——

  日期：——