phenacyl benzyl carbonate | 252979-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenacyl benzyl carbonate
• 英文别名: phenacylbenzyl carbonate；Benzyl phenacyl carbonate；benzyl phenacyl carbonate
• CAS: 252979-72-9
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: GCNUACRYJCPSBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenacyl benzyl carbonate 在 N,N,N',N'-四甲基对苯二胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以72%的产率得到苯甲醇
  参考文献：
  名称：

  Photoreleasable protecting groups on alcohols, phosphates and diacids and the use thereof

  摘要：

  酒精、磷酸酯和二酸衍生物可能通过辐射去保护，所使用的保护基是芳基酰基或杂环芳基酰基。

  公开号：

  US06392089B1
• 作为产物：
  描述：

  2-羟基苯乙酮 、 氯甲酸苄酯 在 吡啶 作用下， 反应 16.0h， 以88%的产率得到phenacyl benzyl carbonate
  参考文献：
  名称：

  Photoreleasable protecting groups on alcohols, phosphates and diacids and the use thereof

  摘要：

  酒精、磷酸酯和二酸衍生物可能通过辐射去保护，所使用的保护基是芳基酰基或杂环芳基酰基。

  公开号：

  US06392089B1

文献信息

• Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids
  作者：Anamitro Banerjee、Kwangjoo Lee、Daniel E. Falvey

  DOI：10.1016/s0040-4020(99)00754-1

  日期：1999.10

  The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10-dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by-products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids. (C) 1999 Elsevier Science Ltd. All rights reserved.