N-(3-methyl-2-butenyl)oxycarbonyl-L-proline benzyl ester | 648910-24-1

• 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: N-(3-methyl-2-butenyl)oxycarbonyl-L-proline benzyl ester
• 英文别名: 2-O-benzyl 1-O-(3-methylbut-2-enyl) (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 648910-24-1
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: DIULLMHILJWKAK-INIZCTEOSA-N

物化性质

• 沸点：
  424.7±45.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(3-methyl-2-butenyl)oxycarbonyl-L-proline benzyl ester 在 碘 、 锌 作用下， 以 甲醇 为溶剂， 反应 5.5h， 以70%的产率得到L-脯氨酸甲酯
  参考文献：
  名称：

  Prenyl carbamates: preparation and deprotection

  摘要：

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.028
• 作为产物：
  描述：

  异戊烯醇 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 124.0h， 生成 N-(3-methyl-2-butenyl)oxycarbonyl-L-proline benzyl ester
  参考文献：
  名称：

  Prenyl carbamates: preparation and deprotection

  摘要：

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.028

文献信息

• One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tetlet.2003.10.058

  日期：2003.12

  The prenyloxycarbonyl (Preoc) moiety was efficiently removed from carbamates to provide the corresponding amines in good to excellent yields (63-88%) by using iodine in methanol followed by treatment of the resulting beta-methoxyiodides by zinc powder. The reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic methyl ethers. (C) 2003 Elsevier Ltd. All rights reserved.
• Prenyl carbamates: preparation and deprotection
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tet.2004.03.028

  日期：2004.5

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.