benzyl 4-pyridyl carbonate | 1417816-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4-pyridyl carbonate
• 英文别名: Benzyl pyridin-4-yl carbonate
• CAS: 1417816-42-2
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: OGTGDMAMSFCZFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 4-pyridyl carbonate 在 甲醇 、 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 反应 0.25h， 以81%的产率得到4-羟基吡啶
  参考文献：
  名称：

  Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature

  摘要：

  A novel protocol for the deprotection of N-benzyloxycarbonyl and O-benzyloxycarbonyl groups by nickel boride generated in situ from NaBH4 and NiCl(2)6H(2)O in methanol at room temperature has been developed to give the corresponding amines and phenols. This protocol is chemoselective as groups like chloro, bromo, amide, ester, pyridine, and tert-butyloxycarbonyl moiety are unaffected under these conditions. The deprotection has also been validated in gram scale reactions, to establish the wider appropriateness of this protocol.

  DOI：

  10.1007/s00706-018-2276-x
• 作为产物：
  描述：

  4-羟基吡啶 、 氯甲酸苄酯 以 二氯甲烷 为溶剂， 生成 benzyl 4-pyridyl carbonate
  参考文献：
  名称：

  4-吡啶基碳酸苄酯在乙腈中的氨解作用：离去基团从 2-吡啶基改成 4-吡啶基对反应活性和反应机理的影响

  摘要：

  过程）在高[胺]区域。这与最近的报道形成对比，即碳酸苄基 2-吡啶基碳酸酯 5 的相应氨解通过强制协同机制进行。建议分子内氢键相互作用迫使 5 的反应通过协同机制进行，因为它可以加速离去基团的排出速率（即 k 的增加

  DOI：

  10.5012/bkcs.2012.33.8.2719

文献信息

• Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature
  作者：Mohit Saroha、Komal Aggarwal、Gaurav Bartwal、Jitender M. Khurana

  DOI：10.1007/s00706-018-2276-x

  日期：2018.12

  A novel protocol for the deprotection of N-benzyloxycarbonyl and O-benzyloxycarbonyl groups by nickel boride generated in situ from NaBH4 and NiCl(2)6H(2)O in methanol at room temperature has been developed to give the corresponding amines and phenols. This protocol is chemoselective as groups like chloro, bromo, amide, ester, pyridine, and tert-butyloxycarbonyl moiety are unaffected under these conditions. The deprotection has also been validated in gram scale reactions, to establish the wider appropriateness of this protocol.
• Aminolysis of Benzyl 4-Pyridyl Carbonate in Acetonitrile: Effect of Modification of Leaving Group from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism
  作者：Ae-Ri Bae、Ik-Hwan Um

  DOI：10.5012/bkcs.2012.33.8.2719

  日期：2012.8.20

  process) in a high [amine] region. This contrasts to the recent report that the corresponding aminolysis of benzyl2-pyridyl carbonate 5 proceeds through a forced concerted mechanism. An intramolecular H-bondinginteraction was suggested to force the reactions of 5 to proceed through a concerted mechanism, since it couldaccelerate the rate of leaving-group expulsion (i.e., an increase in k

  过程）在高[胺]区域。这与最近的报道形成对比，即碳酸苄基 2-吡啶基碳酸酯 5 的相应氨解通过强制协同机制进行。建议分子内氢键相互作用迫使 5 的反应通过协同机制进行，因为它可以加速离去基团的排出速率（即 k 的增加