[(R)-4-(3-Diazo-2-oxo-propyl)-5-oxo-[1,3]dioxolan-4-yl]-acetic acid methyl ester | 199341-38-3

• 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: [(R)-4-(3-Diazo-2-oxo-propyl)-5-oxo-[1,3]dioxolan-4-yl]-acetic acid methyl ester
• 英文别名: methyl 2-[(4R)-4-(3-diazo-2-oxopropyl)-5-oxo-1,3-dioxolan-4-yl]acetate
• CAS: 199341-38-3
• 化学式: C₉H₁₀N₂O₆
• 分子量: 242.188
• InChiKey: YKWAYQIXKUPLDI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(R)-4-(3-Diazo-2-oxo-propyl)-5-oxo-[1,3]dioxolan-4-yl]-acetic acid methyl ester 在 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以88%的产率得到3-[(4R)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]propanoic acid
  参考文献：
  名称：

  Resolution of a citric acid derivative: synthesis of (R)-(−)-homocitric acid-γ-lactone

  摘要：

  Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in greater than or equal to 90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-alpha-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)-homocitric acid utilising an Arndt-Eistert homologation followed by acid catalysed deprotection. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00435-7
• 作为产物：
  描述：

  [(4R)-(+)-4-(2-methoxy-2-oxoethyl)-5-oxo-1,3-dioxolan-4-yl]acetic acid 在 草酰氯 作用下， 以 乙醚 为溶剂， 反应 72.0h， 生成 [(R)-4-(3-Diazo-2-oxo-propyl)-5-oxo-[1,3]dioxolan-4-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Resolution of a citric acid derivative: synthesis of (R)-(−)-homocitric acid-γ-lactone

  摘要：

  Both the (R) and (S) enantiomers of the citric acid derivative 1 have been obtained in greater than or equal to 90% ee via resolution of the racemate by fractional crystallisation of the (S) and (R)-alpha-methylbenzylamine salts respectively. The stereochemistry of (R)-1 has been assigned by its conversion to (R)-(-)-homocitric acid utilising an Arndt-Eistert homologation followed by acid catalysed deprotection. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00435-7

文献信息

• Prokop; Milewska, Polish Journal of Chemistry, 2009, vol. 83, # 7, p. 1317 - 1322
  作者：Prokop、Milewska

  DOI：——

  日期：——