1-O-tert-butyl 2-O-methyl (2S,4R)-4-hydroxy-2-prop-2-enylpyrrolidine-1,2-dicarboxylate | 918820-32-3

• 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: 1-O-tert-butyl 2-O-methyl (2S,4R)-4-hydroxy-2-prop-2-enylpyrrolidine-1,2-dicarboxylate
• CAS: 918820-32-3
• 化学式: C₁₄H₂₃NO₅
• 分子量: 285.34
• InChiKey: ZZRABPDKQOWILY-YGRLFVJLSA-N

物化性质

• 沸点：
  365.8±42.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyl 2-O-methyl (2S,4R)-4-hydroxy-2-prop-2-enylpyrrolidine-1,2-dicarboxylate 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-O-tert-butyl 2-O-methyl (2S,4S)-4-fluoro-2-prop-2-enylpyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Diastereoselectivity in the alkylation of 4-fluoroproline methyl esters

  摘要：

  The reaction of alkylation of cis- and trans-4-fluoro-N-BOC-L-proline methyl esters has been examined by exposing their lithium enolates to a range of alkylating agents. The process showed a high degree of facial diastereoselectivity (except when methyl iodide was used as alkylating agent), invariably giving rise to products bearing the alkyl group in anti with respect to the fluorine atom. A tentative model to account for the observed stereoselectivity is also proposed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.057
• 作为产物：
  描述：

  1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-O-tert-butyl 2-O-methyl (2S,4R)-4-hydroxy-2-prop-2-enylpyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Diastereoselectivity in the alkylation of 4-fluoroproline methyl esters

  摘要：

  The reaction of alkylation of cis- and trans-4-fluoro-N-BOC-L-proline methyl esters has been examined by exposing their lithium enolates to a range of alkylating agents. The process showed a high degree of facial diastereoselectivity (except when methyl iodide was used as alkylating agent), invariably giving rise to products bearing the alkyl group in anti with respect to the fluorine atom. A tentative model to account for the observed stereoselectivity is also proposed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.057

文献信息

• Diastereoselectivity in the alkylation of 4-fluoroproline methyl esters
  作者：Rosanna Filosa、Claude Holder、Yves P. Auberson

  DOI：10.1016/j.tetlet.2006.10.057

  日期：2006.12

  The reaction of alkylation of cis- and trans-4-fluoro-N-BOC-L-proline methyl esters has been examined by exposing their lithium enolates to a range of alkylating agents. The process showed a high degree of facial diastereoselectivity (except when methyl iodide was used as alkylating agent), invariably giving rise to products bearing the alkyl group in anti with respect to the fluorine atom. A tentative model to account for the observed stereoselectivity is also proposed. (c) 2006 Elsevier Ltd. All rights reserved.